7H,10H-呋喃并[2,3,4-cd]萘并[2,1-e]异苯并呋喃-7-酮,十四氢-10-羟基-1,1,4a-三甲基-,(4aS,4bR,6aR,8aR,10R,10aS,10bR,12aS)-(9CI) | 106009-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 中文名称: 7H,10H-呋喃并[2,3,4-cd]萘并[2,1-e]异苯并呋喃-7-酮,十四氢-10-羟基-1,1,4a-三甲基-,(4aS,4bR,6aR,8aR,10R,10aS,10bR,12aS)-(9CI)
• 英文名称: (-)-Dendrillol-1
• 英文别名: (1S,4S,9S,10R,13R,16R,18R,19R)-18-hydroxy-5,5,9-trimethyl-15,17-dioxapentacyclo[11.5.1.01,10.04,9.016,19]nonadecan-14-one
• CAS: 106009-81-8
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: RWVHMWICVBNDMW-HLXKGBKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 7H,10H-呋喃并[2,3,4-cd]萘并[2,1-e]异苯并呋喃-7-酮,十四氢-10-羟基-1,1,4a-三甲基-,(4aS,4bR,6aR,8aR,10R,10aS,10bR,12aS)-(9CI) 在 4-吡咯烷基吡啶 、 三乙胺 作用下， 反应 1.17h， 以90%的产率得到(-)-15α-acetoxyspongian-16-oxo-17-al
  参考文献：
  名称：

  Synthesis and cytotoxic activity of novel C7-Functionalized spongiane diterpenes

  摘要：

  Based on two lead cytotoxic spongiane diterpenes, a new series of C7-oxygenated derivatives were synthesized and evaluated for their antitumor activity in vitro against the cancer cell lines HeLa and HEp-2. In general, introduction of either hvdroxyl or acetoxy groups at C-7 did not improve the resultant cytotoxicity, while the presence of a butyrate ester led to more active compounds (CC50 = 4.0-9.5 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00230-x
• 作为产物：
  描述：

  Δ⁸⁽¹⁴⁾-podocarpen-13-one 在 六甲基磷酰三胺 、 氢氧化钾 、 samarium diiodide 、 二甲基硫 、 sodium methylate 、 臭氧 、 mercury dichloride 、 mercury(II) oxide 、 三甲基乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 98.53h， 生成 7H,10H-呋喃并[2,3,4-cd]萘并[2,1-e]异苯并呋喃-7-酮,十四氢-10-羟基-1,1,4a-三甲基-,(4aS,4bR,6aR,8aR,10R,10aS,10bR,12aS)-(9CI)
  参考文献：
  名称：

  Spongian pentacyclic diterpenes. Stereoselective synthesis of (-)-dendrillol-1

  摘要：

  A formal total synthesis of the spongian diterpene (-)-dendrillol-1 (3), through a consice approach that could be used for the synthesis of other pentacyclic spongian diterpenes, is reported. The synthesis is based on the intramolecular acetalization of an acid-dialdehyde 4, which is prepared from (+)-podocarp-8(14)-en-13-one (5) via a sequence of transformations involving (a) introduction of a latent dialdehyde unit on 5 by photochemical reaction with acetylene, (b) reductive carboxylation at C-13 of photoadduct 6 to obtain acid 18, and (c) elaboration of the dialdehyde moiety at C-8 and C-14 of 18 by ozonolysis. Several procedures that have been examined for the reductive carboxylation at C-13 of 6 are described. A simple three-step procedure to effect the conversion of a podocarp-8-en-13-one system into a C-17-functionalized beyerane compound is also reported.

  DOI：

  10.1021/jo00051a035

文献信息

• Spongian pentacyclic diterpenes. Stereoselective synthesis of (-)-dendrillol-1
  作者：Antonio Abad、Manuel Arno、Ana C. Cunat、M. Luisa Marin、Ramon J. Zaragoza

  DOI：10.1021/jo00051a035

  日期：1992.12

  A formal total synthesis of the spongian diterpene (-)-dendrillol-1 (3), through a consice approach that could be used for the synthesis of other pentacyclic spongian diterpenes, is reported. The synthesis is based on the intramolecular acetalization of an acid-dialdehyde 4, which is prepared from (+)-podocarp-8(14)-en-13-one (5) via a sequence of transformations involving (a) introduction of a latent dialdehyde unit on 5 by photochemical reaction with acetylene, (b) reductive carboxylation at C-13 of photoadduct 6 to obtain acid 18, and (c) elaboration of the dialdehyde moiety at C-8 and C-14 of 18 by ozonolysis. Several procedures that have been examined for the reductive carboxylation at C-13 of 6 are described. A simple three-step procedure to effect the conversion of a podocarp-8-en-13-one system into a C-17-functionalized beyerane compound is also reported.
• Synthesis and cytotoxic activity of novel C7-Functionalized spongiane diterpenes
  作者：Manuel Arnó、Liliana Betancur-Galvis、Miguel A. González、Jelver Sierra、Ramón J. Zaragozá

  DOI：10.1016/s0968-0896(03)00230-x

  日期：2003.7

  Based on two lead cytotoxic spongiane diterpenes, a new series of C7-oxygenated derivatives were synthesized and evaluated for their antitumor activity in vitro against the cancer cell lines HeLa and HEp-2. In general, introduction of either hvdroxyl or acetoxy groups at C-7 did not improve the resultant cytotoxicity, while the presence of a butyrate ester led to more active compounds (CC50 = 4.0-9.5 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.