3-hydroxypropane-1,1-diyl diacetate | 123824-12-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-hydroxypropane-1,1-diyl diacetate
• 英文别名: 3-Hydroxypropylidene diacetate；(1-Acetyloxy-3-hydroxypropyl) acetate
• CAS: 123824-12-4
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: WODMDWCGNJQOMT-UHFFFAOYSA-N

物化性质

• 沸点：
  202.3±20.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxypropane-1,1-diyl diacetate 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,8-trimethyl-6-(2-methylallyl)-2l5-nona-1,8-diene
  参考文献：
  名称：

  Aldophosphamide acetal diacetate and structural analogs: synthesis and cytotoxicity studies

  摘要：

  The synthesis of aldophosphamide acetal diacetate and a number of structural analogues is described. These compounds are designed to undergo biotransformation to the corresponding aldehydes in the presence of carboxylate esterases, enzymes that are ubiquitous in mammalian tissue. Several of these aldehydes can theoretically exist in pseudoequilibrium with the 4-hydroxyoxazaphosphorine tautomers; others lack this capability. The half-lives of the acetals in 0.05 M phosphate buffer, pH 7.4, at 37-degrees-C ranged from 1 to 2 days. In the presence of 2 unit equiv of porcine liver carboxylate esterase, all of the compounds were hydrolyzed with half-lives of less than 1 min. Although closely structurally related, the compounds exhibited a wide range of cytotoxicities to L1210 murine leukemia cells in vitro.

  DOI：

  10.1021/jm00105a030
• 作为产物：
  描述：

  3-(benzyloxy)propane-1,1-diyl diacetate 在 钯 高氯酸 、 calcium carbonate 作用下， 以 乙酸乙酯 为溶剂， 生成 3-hydroxypropane-1,1-diyl diacetate
  参考文献：
  名称：

  Aldophosphamides

  摘要：

  具有结构##STR1##的化合物，其中R为CH.sub.3或C.sub.2 H.sub.5；R.sup.1为NH.sub.2，NHCH.sub.3，NHC.sub.2 H.sub.5，NHC.sub.2 H.sub.4 Cl，N(CH.sub.3).sub.2，N(C.sub.2 H.sub.5).sub.2，N(C.sub.2 H.sub.4 Cl).sub.2，OCH.sub.3，C.sub.2 H.sub.5，CH.sub.3或C.sub.2 H.sub.5，而R.sup.2为N(C.sub.2 H.sub.4 Cl).sub.2或NH C.sub.2 H.sub.4 Cl。这些化合物可用于通过将骨髓与含有足以消除隐匿性白血病克隆细胞的化合物水溶液接触来消除骨髓中的隐匿性白血病克隆细胞。类似地，通过用本说明的化合物处理宿主或宿主器官来消除宿主或宿主器官中的肿瘤细胞。本说明的化合物是稳定的醛磷酰胺类似物，可通过酯酶的作用和随后的E-2消除反应激活，形成丙烯醛和式的磷酰胺芥子：##STR2##其中R为NH.sub.2，NHCH.sub.3，NHC.sub.2 H.sub.5，NHC.sub.2 H.sub.4 Cl，N(CH.sub.3).sub.2，N(C.sub.2 H.sub.5，N(C.sub.2 H.sub.4 Cl).sub.2，OCH.sub.3，OC.sub.2 H.sub.5，CH.sub.3或C.sub.2 H.sub.5。

  公开号：

  US04841085A1

文献信息

• Selective elimination of malignant cells from bone marrow by bis
  申请人：Board of Regents, The University of Texas

  公开号：US05055459A1

  公开（公告）日：1991-10-08

  A method for purging tumor cells from bone marrow of a host, the method comprising extracting bone marrow cells from the host; treating extracted bone marrow cells with a therapeutic level of a compound having the structure: ##STR1## wherein R is CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, t-C.sub.4 H.sub.9 or C.sub.6 H.sub.5 ; R.sup.1 is NH.sub.2, NHCH.sub.3, NHC.sub.2 H.sub.5, NHC.sub.3 H.sub.7, NHC.sub.4 H.sub.9, NHCH.sub.2 CH.sub.2 Cl, NHC.sub.6 H.sub.5, N(CH.sub.3).sub.2, N(C.sub.2 H.sub.5).sub.2, N(C.sub.3 H.sub.7).sub.2, NCH.sub.3 (C.sub.2 H.sub.5), NCH.sub.3 (C.sub.3 H.sub.7), N(CH.sub.2 CH.sub.2 Cl).sub.2, NHOH, NHNHCO.sub.2 CH.sub.2 C.sub.6 H.sub.5, NHNHCO.sub.2 C(CH.sub.3).sub.3, OCH.sub.3, OC.sub.2 H.sub.5, OC.sub.3 H.sub.7, OC.sub.4 H.sub.9, OC.sub.6 H.sub.5, OCH.sub.2 C.sub.6 H.sub.5, CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, C.sub.4 H.sub.9, CH.sub.2 NO.sub.2 or CH.sub.2 NH.sub.2 ; and R.sup.2 is NHCH.sub.2 CH.sub.2 Cl or N(CH.sub.2 Ch.sub.2 Cl).sub.2. Intravascularly infusion of the treated bone marrow cells into the host then serves to reimplant tumor-free marrow cells.

  一种从宿主的骨髓中清除肿瘤细胞的方法，该方法包括提取宿主的骨髓细胞；用具有以下结构的化合物以治疗水平处理提取的骨髓细胞：##STR1## 其中R为CH3、C2H5、C3H7、t-C4H9或C6H5；R1为NH2、NHCH3、NHC2H5、NHC3H7、NHC4H9、NHCH2CH2Cl、NHC6H5、N(CH3)2、N(C2H5)2、N(C3H7)2、NCH3(C2H5)、NCH3(C3H7)、N(CH2CH2Cl)2、NHOH、NHNHCO2CH2C6H5、NHNHCO2C(CH3)3、OCH3、OC2H5、OC3H7、OC4H9、OC6H5、OCH2C6H5、CH3、C2H5、C3H7、C4H9、CH2NO2或CH2NH2；以及R2为NHCH2CH2Cl或N(CH2Ch2Cl)2。然后将经处理的骨髓细胞静脉内注入宿主，以重新植入无肿瘤的骨髓细胞。
• Novel antitumor aldophosphamide analogs
  申请人：Board of Regents, The University of Texas System

  公开号：US05091552A1

  公开（公告）日：1992-02-25

  A compound having the structure: ##STR1## wherein R is CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, t--C.sub.4 H.sub.9 or C.sub.6 H.sub.5 ; R.sup.1 is NH.sub.2, NHCH.sub.3, NHC.sub.2 H.sub.5, NHC.sub.3 H.sub.7, NHC.sub.4 H.sub.9, NHCH.sub.2 CH.sub.2 Cl, NHC.sub.6 H.sub.5, N(CH.sub.3).sub.2, N(C.sub.2 H.sub.5).sub.2, N(C.sub.3 H.sub.7).sub.2, NCH.sub.3 (C.sub.2 H.sub.5), NCH.sub.3 (C.sub.3 H.sub.7), N(CH.sub.2 CH.sub.2 Cl).sub.2, NHOH, NHNHCO.sub.2 CH.sub.2 C.sub.6 H.sub.5, NHNHCO.sub.2 C(CH.sub.3).sub.3, OCH.sub.3, OC.sub.2 H.sub.5, OC.sub.3 H.sub.7, OC.sub.4 H.sub.9, OC.sub.6 H.sub.5, OC.sub.2 C.sub.6 H.sub.5, CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, C.sub.4 H.sub.9, CH.sub.2 NO.sub.2 or CH.sub.2 NH.sub.2 ; and R.sup.2 is NHCH.sub.2 CH.sub.2 Cl or N(CH.sub.2 CH.sub.2 Cl).sub.2. These compounds may be used to eliminate occult leukemic clonogenic cells from bone marrow by contacting the bone marrow with a solution comprising levels of said compound sufficient to eliminate occult leukemic clonogenic cells. Analogously, tumor cells in a host or organ of a host may be eliminated by treatment of the host or host's organ with a compound of this description. Compounds of this description are stable aldophosphamide analogs activatable by the action of an esterase and a subsequent E-2 elimination reaction to form acrolein and a phosphoramidic mustard of the formula: A stable aldophosphamide analog activatable by the action of an esterase and a subsequent spontaneous E-2 elimination reaction to form acrolein and a phosphoramidic mustard, said phosphoramidic mustard having the formula ##STR2## R is NH.sub.2, NHCH.sub.3, NHC.sub.2 H.sub.5, NHC.sub.3 H.sub.7, NHC.sub.4 H.sub.9, NHCH.sub.2 CH.sub.2 Cl, NHC.sub.6 H.sub.5, N(CH.sub.3).sub.2, N(C.sub.2 H.sub.5).sub.2, N(C.sub.3 H.sub.7 (.sub.2, NCH.sub.3 (C.sub.2 H.sub.5), NCH.sub.3 (C.sub.3 H.sub.7), N(CH.sub.2 CH.sub.2 Cl).sub.2, NHOH, NHNHCO.sub.2 CH.sub.2 C.sub.6 H.sub.5, NHNHCO.sub.2 C(CH.sub.3).sub.3, OCH.sub.3, OC.sub.2 H.sub.5, OC.sub.3 H.sub.7, OC.sub.4 H.sub.9, OC.sub.6 H.sub.5, OC.sub.2 C.sub.6 H.sub.5, CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, C.sub.4 H.sub.9, CH.sub.2 NO.sub.2 or CH.sub.2 NH.sub.2 ; and R.sup.1 is NHCH.sub.2 CH.sub.2 Cl or N(CH.sub.2 CH.sub.2 Cl).sub.2.

  一种具有以下结构的化合物：##STR1## 其中 R 是 CH.sub.3、C.sub.2 H.sub.5、C.sub.3 H.sub.7、t--C.sub.4 H.sub.9 或 C.sub.6 H.sub.5；R.sup.1 是 NH.sub.2、NHCH.sub.3、NHC.sub.2 H.sub.5、NHC.sub.3 H.sub.7、NHC.sub.4 H.sub.9、NHCH.sub.2 CH.sub.2 Cl、NHC.sub.6 H.sub.5、N(CH.sub.3).sub.2、N(C.sub.2 H.sub.5).sub.2、N(C.sub.3 H.sub.7).sub.2、NCH.sub.3 (C.sub.2 H.sub.5)、NCH.sub.3 (C.sub.3 H.sub.7)、N(CH.sub.2 CH.sub.2 Cl).sub.2、NHOH、NHNHCO.sub.2 CH.sub.2 C.sub.6 H.sub.5、NHNHCO.sub.2 C(CH.sub.3).sub.3、OCH.sub.3、OC.sub.2 H.sub.5、OC.sub.3 H.sub.7、OC.sub.4 H.sub.9、OC.sub.6 H.sub.5、OC.sub.2 C.sub.6 H.sub.5、CH.sub.3、C.sub.2 H.sub.5、C.sub.3 H.sub.7、C.sub.4 H.sub.9、CH.sub.2 NO.sub.2 或 CH.sub.2 NH.sub.2；而 R.sup.2 是 NHCH.sub.2 CH.sub.2 Cl 或 N(CH.sub.2 CH.sub.2 Cl).sub.2。这些化合物可用于通过将骨髓与含有足够量该化合物的溶液接触来消除骨髓中的潜在白血病克隆细胞。类似地，可以通过用本描述的化合物处理宿主或宿主器官来消除宿主或宿主器官中的肿瘤细胞。本描述的化合物是稳定的醛磷酰胺类似物，可通过酯酶的作用和随后的 E-2 消除反应激活，形成丙烯醛和式为的磷酰胺芥子：一种稳定的醛磷酰胺类似物，可通过酯酶的作用和随后的自发的 E-2 消除反应形成丙烯醛和磷酰胺芥子，所述磷酰胺芥子的式为##STR2## R 是 NH.sub.2、NHCH.sub.3、NHC.sub.2 H.sub.5、NHC.sub.3 H.sub.7、NHC.sub.4 H.sub.9、NHCH.sub.2 CH.sub.2 Cl、NHC.sub.6 H.sub.5、N(CH.sub.3).sub.2、N(C.sub.2 H.sub.5).sub.2、N(C.sub.3 H.sub.7 (.sub.2、NCH.sub.3 (C.sub.2 H.sub.5)、NCH.sub.3 (C.sub.3 H.sub.7)、N(CH.sub.2 CH.sub.2 Cl).sub.2、NHOH、NHNHCO.sub.2 CH.sub.2 C.sub.6 H.sub.5、NHNHCO.sub.2 C(CH.sub.3).sub.3、OCH.sub.3、OC.sub.2 H.sub.5、OC.sub.3 H.sub.7、OC.sub.4 H.sub.9、OC.sub.6 H.sub.5、OC.sub.2 C.sub.6 H.sub.5、CH.sub.3、C.sub.2 H.sub.5、C.sub.3 H.sub.7、C.sub.4 H.sub.9、CH.sub.2 NO.sub.2 或 CH.sub.2 NH.sub.2；而 R.sup.1 是 NHCH.sub.2 CH.sub.2 Cl 或 N(CH.sub.2 CH.sub.2 Cl).sub.2。
• Aldophosphamides
  申请人：Board of Regents, University of Texas System

  公开号：US04841085A1

  公开（公告）日：1989-06-20

  A compound having the structure ##STR1## wherein R is CH.sub.3 or C.sub.2 H.sub.5 1; R.sup.1 is NH.sub.2, NHCH.sub.3, NHC.sub.2 H.sub.5, NHC.sub.2 H.sub.4 Cl, N(CH.sub.3).sub.2, N(C.sub.2 H.sub.5).sub.2, N(C.sub.2 H.sub.4 Cl).sub.2, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.3, or C.sub.2 H.sub.5, and R.sup.2 is N(C.sub.2 H.sub.4 Cl).sub.2 or NH C.sub.2 H.sub.4 Cl. These compounds may be used to eliminate occult leukemic clonogenic cells from bone marrow by contacting the bone marrow with a solution comprising levels of said compound sufficient to eliminate occult leukemic clonogenic cells. Analogously tumor cells in a host or organ of a host may be eliminated by treatment of the host or host's organ with a compound of this description. Compounds of this description are stable aldophosphamide analogs activatable by the action of an esterase and a subsequent E-2 elimination reaction to form acrolein and a phosphoramidic mustard of the formula: ##STR2## wherein R is NH.sub.2, NHCH.sub.3, NHC.sub.2 H.sub.5, NHC.sub.2 H.sub.4 Cl, N(CH.sub.3).sub.2, N(C.sub.2 H.sub.5, N(C.sub.2 H.sub.4 Cl).sub.2, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.3 or C.sub.2 H.sub.5.

  具有结构##STR1##的化合物，其中R为CH.sub.3或C.sub.2 H.sub.5；R.sup.1为NH.sub.2，NHCH.sub.3，NHC.sub.2 H.sub.5，NHC.sub.2 H.sub.4 Cl，N(CH.sub.3).sub.2，N(C.sub.2 H.sub.5).sub.2，N(C.sub.2 H.sub.4 Cl).sub.2，OCH.sub.3，C.sub.2 H.sub.5，CH.sub.3或C.sub.2 H.sub.5，而R.sup.2为N(C.sub.2 H.sub.4 Cl).sub.2或NH C.sub.2 H.sub.4 Cl。这些化合物可用于通过将骨髓与含有足以消除隐匿性白血病克隆细胞的化合物水溶液接触来消除骨髓中的隐匿性白血病克隆细胞。类似地，通过用本说明的化合物处理宿主或宿主器官来消除宿主或宿主器官中的肿瘤细胞。本说明的化合物是稳定的醛磷酰胺类似物，可通过酯酶的作用和随后的E-2消除反应激活，形成丙烯醛和式的磷酰胺芥子：##STR2##其中R为NH.sub.2，NHCH.sub.3，NHC.sub.2 H.sub.5，NHC.sub.2 H.sub.4 Cl，N(CH.sub.3).sub.2，N(C.sub.2 H.sub.5，N(C.sub.2 H.sub.4 Cl).sub.2，OCH.sub.3，OC.sub.2 H.sub.5，CH.sub.3或C.sub.2 H.sub.5。
• FARQUHAR, DAVID;WANG, YUQIANG
  作者：FARQUHAR, DAVID、WANG, YUQIANG

  DOI：——

  日期：——
• WANG, YUQIANG;FARQUHAR, DAVID, J. MED. CHEM., 34,(1991) N, C. 197-203
  作者：WANG, YUQIANG、FARQUHAR, DAVID

  DOI：——

  日期：——