3β-hydroxy-6-oxo-7-oxa-B-homo-5α-cholestane | 86401-29-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-hydroxy-6-oxo-7-oxa-B-homo-5α-cholestane
• 英文别名: 3β-hydroxy-B-homo-7-oxa-5α-cholestan-6-one；(1S,2R,5S,7S,11S,12S,15R,16R)-5-hydroxy-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one
• CAS: 86401-29-8；20104-91-0
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: YRLYHWWOZFZBDO-ZNCJEFCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-6-oxo-7-oxa-B-homo-5α-cholestane 在 Collins reagent 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 6-oxo-7-oxa-B-homo-5α-cholest-3-one thiosemicarbazone
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some steroidal lactone compounds

  摘要：

  Using cholesterol as starting material, some steroidal lactone compounds with the structures of 3-substituted-6-oxo-7-oxa-B-homo-cholestane or 3-substituted-7-oxo-6-oxa-B-homo-cholestane were synthesized by oxidation, reduction, Baeyer-Villiger reaction and condensation reaction. The cytotoxicity of these compounds against MGC 7901 (human gastric carcinoma), HeLa (human cervical carcinoma) and SMMC 7404 (human liver carcinoma) cells was investigated. Our results showed that the synthesized compounds displayed a distinct cytotoxicity against these cancer cells. In particular, compounds 8 and 9 have similar cytotoxic capability as cisplatin does. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.11.013
• 作为产物：
  描述：

  胆固醇 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 3β-hydroxy-6-oxo-7-oxa-B-homo-5α-cholestane
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some steroidal lactone compounds

  摘要：

  Using cholesterol as starting material, some steroidal lactone compounds with the structures of 3-substituted-6-oxo-7-oxa-B-homo-cholestane or 3-substituted-7-oxo-6-oxa-B-homo-cholestane were synthesized by oxidation, reduction, Baeyer-Villiger reaction and condensation reaction. The cytotoxicity of these compounds against MGC 7901 (human gastric carcinoma), HeLa (human cervical carcinoma) and SMMC 7404 (human liver carcinoma) cells was investigated. Our results showed that the synthesized compounds displayed a distinct cytotoxicity against these cancer cells. In particular, compounds 8 and 9 have similar cytotoxic capability as cisplatin does. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.11.013

文献信息

• Remote substituent effect on the regioselectivity in the baeyer-villiger oxidation of 5α-cholestan-6-one derivatives
  作者：Suguru Takatsuto、Nobuo Ikekawa

  DOI：10.1016/s0040-4039(00)81564-6

  日期：——

  The regioselectivity in the Baeyer-Villiger oxidation of 5α-cholestan-6-one derivatives was markedly affected by the substituents at C-1, 2 or 3 position which were located at γ or δ position from the reaction center c-6.

  5α-胆甾烷-6-一衍生物在Baeyer-Villiger氧化中的区域选择性受到位于距反应中心c-6的γ或δ位置的C-1、2或3位取代基的显着影响。