methyl 4,4-diethoxycyclobut-1-ene-1-carboxylate | 78001-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,4-diethoxycyclobut-1-ene-1-carboxylate
• 英文别名: methyl 4,4-diethoxy-1-cyclobutenecarboxylate；methyl 4,4-diethoxycyclobutene-1-carboxylate
• CAS: 78001-78-2
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: HAFDSUAODJKUIS-UHFFFAOYSA-N

物化性质

• 沸点：
  251.9±40.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4,4-diethoxycyclobut-1-ene-1-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (1R,4S)-2,2-Diethoxy-4-(6-methoxy-purin-9-yl)-cyclobutanecarboxylic acid methyl ester
  参考文献：
  名称：

  Carbocyclic Oxetanocins Lacking the C-3‘ Methylene

  摘要：

  Using the observation that the side effects of aristeromycin (carbocyclic adenosine) were reduced by removing the methylene at the center in aristeromycin where phosphorylation occurs, derivatives of carbocyclic oxetanocin A (4a), oxetanocin G (4b), and 2-aminooxetanocin A (16) lacking the 3'-methylene have been prepared in racemic form. The only viruses for which an appreciable inhibitory effect of the compounds (minimum inhibitory concentration ranging from 1 to 40 mu g/mL) was noted were herpes simplex virus type 1 (HSV-1) and varicella-zoster virus (VZV). However, when directly compared for their antiviral potency against HSV-1 with their parents oxetanocin A and oxetanocin G, compounds 4a and 4b proved clearly less active.

  DOI：

  10.1021/jm960770e

文献信息

• Process for preparation of intermediates of carbocyclic nucleoside
  申请人：Bristol-Myers Squibb Company

  公开号：US05153352A1

  公开（公告）日：1992-10-06

  A compound of the formula: ##STR1## wherein A is a purin-9-yl group, a heterocyclic isostere of a purin-9-yl group, a pyrimidin-1-yl group or a heterocyclic isostere of a pyrimidin-1-yl group; E is hydrogen, --CH.sub.2 OH or --OH; and G and D are independently selected from hydrogen, C.sub.1 to C.sub.10 alkyl, --OH, --CH.sub.2 OH, --CH.sub.2 OR.sub.20 wherein R.sub.20 is C.sub.1 to C.sub.6 alkyl, --CH.sub.2 OC(O)R.sub.21 wherein R.sub.21 is C.sub.1 to C.sub.10 alkyl, --CH.sub.2 OC(O)CH(R.sub.22)(NHR.sub.23) wherein R.sub.22 is the side chain of any of the naturally occuring amino acids and R.sub.23 is hydrogen or --C(O)CH(R.sub.24)(NH.sub.2) wherein R.sub.24 is the side chain of any of the naturally occuring amino acids, --CH.sub.1 SH, --Ch.sub.2 Cl, --Ch.sub.2 F, --CH.sub.2 Br, --CH.sub.2 I, --C(O)H, --CH.sub.2 CN, --CH.sub.2 N.sub.3, --CH.sub.2 NR.sub.1 R.sub.2, --CO.sub.2 R.sub.1, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH.sub.2 OR.sub.20 wherein R.sub.20 is as defined above, --CH.sub.2 CH.sub.2 OC(O)R.sub.21 wherein R.sub.21 is as defined above, --CH.sub.2 CH.sub.2 OC(O)CH(R.sub.22)(NHR.sub.23) wherein R.sub.22 and R.sub.23 are as defined above, --CH.sub.2 CH.sub.2 PO.sub.3 H.sub.2, --Ch.sub.2 OPO.sub.3 H.sub.2, --OCH.sub.2 PO.sub.3 H.sub.2 and --CH.sub.2 CO.sub.2 R.sub.3 wherein R.sub.1 and R.sub.2 are independently selected from hydrogen and C.sub.1 to C.sub.10 alkyl and R.sub.3 is hydrogen, C.sub.1 to C.sub.10 alkyl, carboxyalkyl or aminoalkyl; or a pharmaceutically acceptable salt thereof.

  该化合物的化学式为：##STR1## 其中A是嘌呤-9-基团，嘌呤-9-基团的杂环同分异构体，嘧啶-1-基团或嘧啶-1-基团的杂环同分异构体；E是氢，-CH.sub.2 OH或-OH；G和D分别选择自氢，C.sub.1到C.sub.10烷基，-OH，-CH.sub.2 OH，-CH.sub.2 OR.sub.20，其中R.sub.20是C.sub.1到C.sub.6烷基，-CH.sub.2 OC(O)R.sub.21，其中R.sub.21是C.sub.1到C.sub.10烷基，-CH.sub.2 OC(O)CH(R.sub.22)(NHR.sub.23)，其中R.sub.22是任何天然氨基酸的侧链，R.sub.23是氢或-C(O)CH(R.sub.24)(NH.sub.2)，其中R.sub.24是任何天然氨基酸的侧链，-CH.sub.1 SH，-Ch.sub.2 Cl，-Ch.sub.2 F，-CH.sub.2 Br，-CH.sub.2 I，-C(O)H，-CH.sub.2 CN，-CH.sub.2 N.sub.3，-CH.sub.2 NR.sub.1 R.sub.2，-CO.sub.2 R.sub.1，-CH.sub.2 CH.sub.2 OH，-CH.sub.2 CH.sub.2 OR.sub.20，其中R.sub.20如上定义，-CH.sub.2 CH.sub.2 OC(O)R.sub.21，其中R.sub.21如上定义，-CH.sub.2 CH.sub.2 OC(O)CH(R.sub.22)(NHR.sub.23)，其中R.sub.22和R.sub.23如上定义，-CH.sub.2 CH.sub.2 PO.sub.3 H.sub.2，-Ch.sub.2 OPO.sub.3 H.sub.2，-OCH.sub.2 PO.sub.3 H.sub.2和-CH.sub.2 CO.sub.2 R.sub.3，其中R.sub.1和R.sub.2分别选择自氢和C.sub.1到C.sub.10烷基，R.sub.3是氢，C.sub.1到C.sub.10烷基，羧基烷基或氨基烷基；或其药用可接受盐。
• Carbocyclic nucleoside analogs
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0366059A2

  公开（公告）日：1990-05-02

  A compound of the formula: wherein A is a purin-9-yl group, a heterocyclic isostere of a purin-9-yl group, a pyrimidin-1-yl group or a heterocyclic isostere of a pyrimidin-1-yl group; E is hydrogen, -CH20H or -OH; and G and D are independently selected from hydrogen, C1 to C10 alkyl, -OH, -CH20H, -CH2OR20 wherein R20 is C1 to C6 alkyl, -CH2OC(O)R21 wherein R21 is C1 to C10 alkyl, -CH2OC(O)CH(R22)(NHR23) wherein R22 is the side chain of any of the naturally occuring amino acids and R23 is hydrogen or -C(O)CH(R24)(NH2) wherein R24 is the side chain of any of the naturally occuring amino acids, -CH2SH, -CHzCI, -CH2F, -CH2Br, -CH2I, -C-(O)H, -CH2CN, -CH2N3, -CH2NR1R2, -CO2R1, -CH2CH20H, -CH2CH2OR20 wherein R20 is as defined above, -CH2CH20C(O)R21 wherein R21 is as defined above -CH2CH20C(O)CH(R22)(NHR23) wherein R22 and R23 are as defined above -CH2CH2PO3H2, -CH2OPO3H2, -OCH2PO3H2 and -CH2CO2R3 wherein R, and R2 are independently selected from hydrogen and C1 to C10 alkyl and R3 is hydrogen, C1 to C10 alkyl carboxyalkyl or aminoalkyl; or a pharmaceutically acceptable salt thereof.

  式中的化合物： 其中 A 是嘌呤-9-基团、嘌呤-9-基团的杂环异构体、嘧啶-1-基团或嘧啶-1-基团的杂环异构体；E 是氢、-CH20H 或 -OH；G和D独立地选自氢、C1至C10烷基、-OH、-CH20H、-CH2OR20（其中R20为C1至C6烷基）、-CH2OC(O)R21（其中R21为C1至C10烷基）、-CH2OC(O)CH(R22)(NHR23)，其中 R22 是任何天然氨基酸的侧链，R23 是氢或-C(O)CH(R24)(NH2)，其中 R24 是任何天然氨基酸的侧链，-CH2SH、-CHzCI、-CH2F、-CH2Br、-CH2I、-C-(O)H、-CH2CN、-CH2N3、-CH2NR1R2、-CO2R1、-CH2CH20H、-CH2CH2OR20（其中 R20 如上定义）、-CH2CH20C(O)R21（其中 R21 如上定义）、-CH2CH20C(O)CH(R22)(NHR23)（其中 R22 和 R23 如上定义）、-CH2CH2PO3H2、-CH2OPO3H2、-OCH2PO3H2 和 -CH2CO2R3 其中 R 和 R2 独立地选自氢和 C1 至 C10 烷基，R3 为氢、C1 至 C10 烷基羧基或氨基烷基；或其药学上可接受的盐。
• Synthesis of (.+-.)-fomannosin
  作者：M. F. Semmelhack、Shuji Tomoda

  DOI：10.1021/ja00399a057

  日期：1981.5
• US5153352A
  申请人：——

  公开号：US5153352A

  公开（公告）日：1992-10-06
• US5246931A
  申请人：——

  公开号：US5246931A

  公开（公告）日：1993-09-21