(R,12Z,15Z)-1,2-dihydroxyhenicosa-12,15-dien-4-one | 1005326-87-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R,12Z,15Z)-1,2-dihydroxyhenicosa-12,15-dien-4-one
• 英文别名: (2R,12Z,15Z)-1,2-dihydroxyhenicosa-12,15-dien-4-one
• CAS: 1005326-87-3
• 化学式: C₂₁H₃₈O₃
• 分子量: 338.531
• InChiKey: FVSGCMLHPLCPEU-DSADLTMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,12Z,15Z)-1,2-dihydroxyhenicosa-12,15-dien-4-one 、 氯化异氰盐酸盐 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以11%的产率得到(R)-(12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl isonicotinate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells

  摘要：

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.006
• 作为产物：
  描述：

  亚油酸甲酯 在 N-[3,5-双(三氟甲基)苯基]-N'-[(8a,9S)-6'-甲氧基-9-金鸡宁]硫脲 、 N,N-二异丙基乙胺 、 lithium chloride 、 lithium diisopropyl amide 、 苯硼酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 60.25h， 生成 (R,12Z,15Z)-1,2-dihydroxyhenicosa-12,15-dien-4-one
  参考文献：
  名称：

  Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells

  摘要：

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.006

文献信息

• Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons
  作者：De Run Li、Andiappan Murugan、J. R. Falck

  DOI：10.1021/ja076802c

  日期：2008.1.1

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
• Synthesis and in vitro evaluation of analogues of avocado-produced toxin (+)-(R)-persin in human breast cancer cells
  作者：Darby G. Brooke、Elizabeth J. Shelley、Caroline G. Roberts、William A. Denny、Robert L. Sutherland、Alison J. Butt

  DOI：10.1016/j.bmc.2011.10.006

  日期：2011.12

  A structure-activity study of several new synthetic analogues of the avocado-produced toxin persin has been conducted, with compounds being evaluated for their cytostatic and pro-apoptotic effects in human breast cancer cells. A 4-pyridinyl derivative demonstrated activity comparable to that of the natural product, suggesting future directions for exploration of structure-activity relationships. (C) 2011 Elsevier Ltd. All rights reserved.