[(1S,2R,4S,4aS,5S,8Z,10E,12aS)-4-acetyloxy-2-hydroxy-11-[(2R)-1-methoxy-1-oxopropan-2-yl]-1,4a,8-trimethyl-12-oxo-1,2,3,4,5,6,7,12a-octahydrobenzo[10]annulen-5-yl] butanoate | 1262440-00-5

• 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: [(1S,2R,4S,4aS,5S,8Z,10E,12aS)-4-acetyloxy-2-hydroxy-11-[(2R)-1-methoxy-1-oxopropan-2-yl]-1,4a,8-trimethyl-12-oxo-1,2,3,4,5,6,7,12a-octahydrobenzo[10]annulen-5-yl] butanoate
• CAS: 1262440-00-5
• 化学式: C₂₇H₄₀O₈
• 分子量: 492.61
• InChiKey: PFZIKZPNVHMBFU-MPKLFVJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(1S,2R,4S,4aS,5S,8Z,10E,12aS)-4-acetyloxy-2-hydroxy-11-[(2R)-1-methoxy-1-oxopropan-2-yl]-1,4a,8-trimethyl-12-oxo-1,2,3,4,5,6,7,12a-octahydrobenzo[10]annulen-5-yl] butanoate 以 氘代甲醇 为溶剂， 反应 120.0h， 生成 briareolate ester G
  参考文献：
  名称：

  Bioactive Diterpenoid Containing a Reversible “Spring-Loaded” (E,Z)-Dieneone Michael Acceptor

  摘要：

  Three new briarane diterpenoids, briareolate esters L-N (1-3), have been isolated from a gorgonian Briareum asbestinum. Briareolate esters L (1) and M (2) are the first natural products possessing a 10-membered macrocyclic ring with a (E,Z)-dieneone and exhibit growth inhibition activity against both human embryonic stem cells (BG02) and a pancreatic cancer cell line (BxPC-3). Briareolate ester L (1) was found to contain a "spring-loaded" (E,Z)-dieneone Michael acceptor group that can form a reversible covalent bond to model sulfur-based nucleophiles.

  DOI：

  10.1021/ol201443k
• 作为产物：
  描述：

  在 苯硫酚 作用下， 以 氘代甲醇 为溶剂， 生成 [(1S,2R,4S,4aS,5S,8Z,10E,12aS)-4-acetyloxy-2-hydroxy-11-[(2R)-1-methoxy-1-oxopropan-2-yl]-1,4a,8-trimethyl-12-oxo-1,2,3,4,5,6,7,12a-octahydrobenzo[10]annulen-5-yl] butanoate
  参考文献：
  名称：

  Bioactive Diterpenoid Containing a Reversible “Spring-Loaded” (E,Z)-Dieneone Michael Acceptor

  摘要：

  Three new briarane diterpenoids, briareolate esters L-N (1-3), have been isolated from a gorgonian Briareum asbestinum. Briareolate esters L (1) and M (2) are the first natural products possessing a 10-membered macrocyclic ring with a (E,Z)-dieneone and exhibit growth inhibition activity against both human embryonic stem cells (BG02) and a pancreatic cancer cell line (BxPC-3). Briareolate ester L (1) was found to contain a "spring-loaded" (E,Z)-dieneone Michael acceptor group that can form a reversible covalent bond to model sulfur-based nucleophiles.

  DOI：

  10.1021/ol201443k

文献信息

• Bioactive Diterpenoid Containing a Reversible “Spring-Loaded” (<i>E,Z</i>)-Dieneone Michael Acceptor
  作者：Prasoon Gupta、Upasana Sharma、Thomas C. Schulz、Eric S. Sherrer、Amanda B. McLean、Allan J. Robins、Lyndon M. West

  DOI：10.1021/ol201443k

  日期：2011.8.5

  Three new briarane diterpenoids, briareolate esters L-N (1-3), have been isolated from a gorgonian Briareum asbestinum. Briareolate esters L (1) and M (2) are the first natural products possessing a 10-membered macrocyclic ring with a (E,Z)-dieneone and exhibit growth inhibition activity against both human embryonic stem cells (BG02) and a pancreatic cancer cell line (BxPC-3). Briareolate ester L (1) was found to contain a "spring-loaded" (E,Z)-dieneone Michael acceptor group that can form a reversible covalent bond to model sulfur-based nucleophiles.