苄基乙烯基碳酸酯 | 113150-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苄基乙烯基碳酸酯
• 英文名称: benzyl vinyl carbonate
• 英文别名: benzyl ethenyl carbonate
• CAS: 113150-67-7
• 化学式: C₁₀H₁₀O₃
• mdl: MFCD07186297
• 分子量: 178.188
• InChiKey: HVSHJHHDLLAIEB-UHFFFAOYSA-N

物化性质

• 沸点：
  112-115 °C(Press: 4 Torr)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苄基乙烯基碳酸酯 在 四氮唑 、 hormone-sensitive lipase 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 17.33h， 生成 (S)-2-(benzyloxycarbonyl)amino-2-(benzyloxycarbonyloxy)methyl-1-(dibenzyl)phosphoryloxy-4-(4-octylphenyl)butane
  参考文献：
  名称：

  免疫抑制性FTY720-磷酸酯的对映异构体的不对称合成和生物学评估。

  摘要：

  完成了对免疫抑制性FTY720-磷酸酯（2）的两种对映异构体的实际不对称合成，并通过药理学评估了该对映异构体。几种脂肪酶与N-乙酰基FTY720（3）或N-苄氧基羰基FTY720（7）结合乙酸乙烯酯或碳酸苄基乙烯基酯作为酰基供体，对O-酰化显示出显着的活性和对映选择性。使用脂肪酶催化的酰化作用作为关键步骤的合成产生了对映体纯的（> 99.5％ee）对映体，数量为2克。（2）的（S）-异构体比（R）-2具有更强的与S1P（1,3,4,5）的结合亲和力和对淋巴细胞向S1P迁移的抑制活性，这表明2的（S）-异构体对给药1后的免疫抑制活性。

  DOI：

  10.1016/j.bmc.2004.10.008
• 作为产物：
  描述：

  氯甲酸乙烯酯 、 苯甲醇 在 吡啶 作用下， 反应 0.5h， 以75%的产率得到苄基乙烯基碳酸酯
  参考文献：
  名称：

  Vinyl carbonates as novel alkoxycarbonylation reagents in enzymatic synthesis of carbonates.

  摘要：

  Carbonates could be obtained by enzymatic alkoxycarbonylation from vinyl carbonates, which are easily prepared from vinyl chloroformate. The reaction was catalyzed by Candida antarctica lipases, SP 435 and SP 435 A. The method could be also used for the synthesis of carbamates. When racemic alcohols were used, lipase catalyzed their resolution, and chiral carbonates were obtained with different enantiomeric excesses depending upon the structure of the alcohol.

  DOI：

  10.1016/s0040-4020(01)88237-5

文献信息

• Nonaqueous Biocatalytic Synthesis of New Cytotoxic Doxorubicin Derivatives:  Exploiting Unexpected Differences in the Regioselectivity of Salt-Activated and Solubilized Subtilisin
  作者：David H. Altreuter、Jonathan S. Dordick、Douglas S. Clark

  DOI：10.1021/ja015977y

  日期：2002.3.1

  a salt-activated enzyme. Using AOT-SC catalysis, four unique selectively acylated DOX analogues were generated, and KCl-SC was used to prepare DOX derivatives acylated at the alternative sites. Cytotoxicities of select derivatives were evaluated against the MCF7 breast cancer cell line (DOX IC50 = 27 nM) and its multidrug-resistant sub-line, MCF7-ADR (DOX IC50 = 27 muM). The novel derivative 14-(2-thiophene

  两种酶，毛毛虫脂肪酶和枯草杆菌蛋白酶 Carlsberg (SC)，催化阿霉素 (DOX) 的非水酰化。与未处理的酶相比，甲苯中丁酸乙烯酯在 C-14 位的 DOX 酰化率通过与气溶胶 OT (AOT) 离子配对的脂肪酶高 25 倍，由 98% (w /w) KCl 共冻干（分别为 3.21 和 0.67 μmol/min g-脂肪酶，相对于 0.13 μmol/min g-脂肪酶）。颗粒枯草杆菌蛋白酶 (SC) 几乎不能进行 DOX 酰化，但离子对 SC (AOT-SC) 以 2.85 μmol/min g-蛋白酶的速率催化酰化。M. javanicus 制剂、AOT-SC 和 SC 专门酰化 DOX 的 C14 伯羟基。SC 与 98% (w/w) KCl 的共冻干扩大了酶的区域特异性，使得 KCl-SC 额外酰化了 C4' 羟基和 C3' 胺基团。使用 KCl-SC 的 DOX 总转化率为
• Simple one-step preparations of vinylic carbonates from aldehydes
  作者：R. A. Olofson、Dang Vu Anh、David S. Morrison、Paul F. De Cusati

  DOI：10.1021/jo00288a001

  日期：1990.1
• OLOFSON, R. A.;DANG, VU ANH;MORRISON, DAVID S.;DE, CUSATI PAUL F., J. ORG. CHEM., 55,(1990) N, C. 1-3
  作者：OLOFSON, R. A.、DANG, VU ANH、MORRISON, DAVID S.、DE, CUSATI PAUL F.

  DOI：——

  日期：——
• [EN] METHODS FOR PREPARING DOXORUBICIN DERIVATIVES<br/>[FR] PROCEDES PERMETTANT DE PREPARER DES DERIVES DE DOXORUBICINE
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2003057687A1

  公开（公告）日：2003-07-17

  The present invetion relates to a process for preparation of a product compound of formula (I), where R1 is an acyl group. The process involves reacting a starting compound of formula (II), with an activated acyl donor compound in the presence of a non-chemically modified lipase, under conditions effective to produce the product compound.
• [EN] METHODS FOR PREPARING ANTHRACYCLINONE DERIVATIVES AND ANTHRACYCLINONE DERIVATIVES PER SE<br/>[FR] METHODES PERMETTANT DE PREPARER DES DERIVES D'ANTHRACYCLINONE ET LESDITS DERIVES D'ANTHRACYCLINONE
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2003057896A1

  公开（公告）日：2003-07-17

  The present invention relates to a process for preparation of a product compound of the Formula (I), where R1 is an acyl group, R2 is H, an N-alkylated amino sugar, or a non-basic sugar moiety, and R3 is H, OH, or OCH3. The process involves reacting a starting compound of the Formula (II) with an acyl donor compound in the presence of a non-chemically modified lipase, under conditions effective to produce the product compound. Another aspect of the present invention relates to a compound of the following Formula (III), where: R1 is an acyl radical of a carboxylic acid selected from the group consisting of: polyethylene glycol acetic acid and polyunsaturated fatty acid; and R2 = 2,6-dideoxy-2-fluoro-α-talopyranosyl; 3-trifluoroacetylamino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl; or 3-deamino-3-(2'-pyrroline-1'-yl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl; or a pharmaceutically acceptable salt thereof. The present invention also relates to a compound of the Formula (IV) where n is 4 or 5, or a pharmaceutically acceptable salt thereof. Another aspect of the present invention relates to a compound of the Formula (V) where: R1 is an acyl group, R2 is 3-substituted allyloxycarbonylamino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl, R3 is H, OH, or OCH3.