(1R,2R,6R,8R,12S,13R,14S,16S,17R)-12,16-dihydroxy-4,4,9,9,13-pentamethyl-18-methylidene-3,5-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecan-19-one | 78536-39-7

• 英文名称: (1R,2R,6R,8R,12S,13R,14S,16S,17R)-12,16-dihydroxy-4,4,9,9,13-pentamethyl-18-methylidene-3,5-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecan-19-one
• CAS: 78536-39-7
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: CQGAPHXZMVIJSY-VJDNWQJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,6R,8R,12S,13R,14S,16S,17R)-12,16-dihydroxy-4,4,9,9,13-pentamethyl-18-methylidene-3,5-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecan-19-one 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 mineral oil 为溶剂， 反应 24.5h， 生成 (1S,4aR,6R,6aR,9S,10S,11aS,11bR,12R)-6,12-dihydroxy-1,10-dimethoxy-4,4,11b-trimethyl-8-methylenedodecahydro-6a,9-methanocyclohepta[a]naphthalen-7(1H)-one
  参考文献：
  名称：

  Efficient transformation of 7,14-dihydroxy-ent-kaurenes to novel ent-abietanes having cis-fused α-methylene γ-lactones under Mitsunobu reaction conditions and their cytotoxicities

  摘要：

  Transformation of plant-origin 7,14-dihydroxy-ent-kaurenes to ent-abietanes having a cis-fused alpha-methylene gamma-lactones was accomplished efficiently under the Mitsunobu reaction conditions. The yields of the desired products were apparently influenced by the steric hindrance at C-1. The cytotoxic activity on P388 murine leukemia cells of the ent-abietanes having cis-fused alpha-methylene gamma-lactones produced were assayed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.082
• 作为产物：
  描述：

  excisanin B 在 sodium hydroxide 、 copper(II) sulfate 作用下， 生成 (1R,2R,6R,8R,12S,13R,14S,16S,17R)-12,16-dihydroxy-4,4,9,9,13-pentamethyl-18-methylidene-3,5-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecan-19-one
  参考文献：
  名称：

  Sun, Han-dong; Sun, Xi-chang; Lin, Zhon-wen, Chemistry Letters, 1981, p. 753 - 756

  摘要：

  DOI：

文献信息

• Efficient synthesis of novel cytotoxic cis-fused α-methylene γ-lactones from 7,14-dihydroxy-ent-kaurenes by transformation under Mitsunobu reaction conditions
  作者：Yutaka Aoyagi、Ming-Yu Gui、Yong-Ri Jin、Xu-Wen Li、Takeshi Noguchi、Haruhiko Fukaya、Tomoyo Hasuda、Koichi Takeya

  DOI：10.1016/j.tetlet.2003.12.041

  日期：2004.2

  14-dihydroxy-ent-kaurenes such as excisanin A (8), kamebanin (9), and kamebakaurin (10), which are abundant in plants of the genus Rabdosia species (Labiatae), to ent-abietanes was accomplished under the Mitsunobu reaction conditions. The δ, ε-unsaturated cis-fused α-methylene γ-lactones (17, 18, and 25) thus prepared showed a moderate cytotoxic activity on P388 murine leukemia cells.

  的7,14二羟基容易转化ENT -kaurenes如excisanin A（8），kamebanin（9），和kamebakaurin（10），这是在丰富属植物香茶菜物种（唇形科），以ENT -abietanes是在Mitsunobu反应条件下完成。的δ，ε -不饱和顺-融合α亚甲基γ内酯（17，18，和25）如此制备显示对P388鼠白血病细胞温和的细胞毒性活性。