ethylene ketal of 2,3-epoxy-bicyclo<3.3.0>octane-7-one | 77532-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethylene ketal of 2,3-epoxy-bicyclo<3.3.0>octane-7-one
• 英文别名: ethylene ketal of 2,3-epoxy-bicyclo[3.3.0]octane-7-one；(1'S,2'S,4'R,6'R)-spiro[1,3-dioxolane-2,8'-3-oxatricyclo[4.3.0.02,4]nonane]
• CAS: 77532-51-5；77551-65-6；108692-53-1
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: XJLFCNVYYFQEGU-XAVMHZPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.99
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethylene ketal of 2,3-epoxy-bicyclo<3.3.0>octane-7-one 在 正丁基锂 、 硫酸 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 5E-9a-carba-14(1-hydroxy-4-isopropylidenecyclohexyl)-13,14-dehydro prostaglandin I₂
  参考文献：
  名称：

  Synthesis and anti-aggregative activity of novel ω-achiral carba-analogues of prostacyclin

  摘要：

  Novel stable bicyclo[3.3.0]octanic and bicyclo[4.2.0]octanic 13,14-didehydrocarbacyclins 1a-c, 2a bearing an achiral cyclohexanoic group at C-14 were synthesized. These analogues have been characterized by C-13 NMR spectroscopy. Compounds 1a-c and 2a were tested on rabbit and human platelet-rich blood plasma and 1a-c on rat stomach and guinea pig trachea smooth muscles. E-isomers of 1a-b were found to be less active but more selective than PGE1. The anti-aggregative potency of E-isomer of compounds 1a-b and Z-isomer of 2a on human platelets was 10(-1) - 10(-2) of the activity of PGE1. The contractive activity of bicyclo[3.3.0]octane analogues 1a-c was 10(-3) - 10(-4) of that for PGE1. On platelets and guinea-pig trachea 5E-isomers of the Corresponding analogues were more potent, whereas on rat stomach muscle 5Z-isomers were.

  DOI：

  10.1016/0223-5234(92)90104-9
• 作为产物：
  描述：

  bicyclo[2.2.2]oct-2-ene 在 氢氧化钾 、 Nafion-TMS 、 五氯化磷 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 原甲酸三甲酯 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 生成 ethylene ketal of 2,3-epoxy-bicyclo<3.3.0>octane-7-one
  参考文献：
  名称：

  Demuth, Martin; Schaffner, Kurt, Angewandte Chemie, 1982, vol. 94, # 11, p. 809 - 825

  摘要：

  DOI：

文献信息

• Regio- and Stereoselective Functionalizations of Tricyclo [3.3.0.02,8]octan-3-one, a Potential Synthon for Polycyclopentanoid Terpenes and Prostacyclin Analogs. Preliminary Communication
  作者：Martin Demuth、Sosale Chandrasekhar、Koichi Nakano、Palaykotai R. Raghavan、Kurt Schaffner

  DOI：10.1002/hlca.19800630837

  日期：1980.12.10

  transformation of tricyclo [3.3.0.02,8]octan-3-one (1) have been carried out in order to explore its potential utility as a versatile synthon for polycyclopentanoid terpenes and prostacyclin analogs. Various functionalizations of rings A and B and annulation of a third ring C were achieved in generally high yields. The system provides for a large measure of regio- and stereoselective reaction control

  为了探索其作为多环戊烷萜烯和前列环素类似物的通用合成子的潜在用途，已进行了三环[3.3.0.0 2,8 ] octan -3-one （1）的化学转化。通常以高收率实现环A和B的各种官能化以及第三环C的环化。该系统提供了大量的区域和立体选择性反应控制。
• PARVE, O.;PALS, ANNE;LYXMUS, M.;VYALIMYAEH, T.;LAXE, LIL;LOPP, M.;LILLE, +, IZV. AN EHSSR. XIMIYA, 38,(1989) N, S. 112-118
  作者：PARVE, O.、PALS, ANNE、LYXMUS, M.、VYALIMYAEH, T.、LAXE, LIL、LOPP, M.、LILLE, +

  DOI：——

  日期：——
• LOPP, M. I.;BERGMANN, M. A.;BEZUGLOV, V. V.;VYALIMYAEH, T. K.;LOPP, A. X.+, BIOORGAN. XIMIYA, 14,(1988) N 6, 834-838
  作者：LOPP, M. I.、BERGMANN, M. A.、BEZUGLOV, V. V.、VYALIMYAEH, T. K.、LOPP, A. X.+

  DOI：——

  日期：——