2,4,6,8-壬四烯酸,7-甲基-9-(2,6,6-三甲基-1-环己烯-1-基)-,(2E,4E,6Z,8E)- | 131235-61-5

• 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
• 中文名称: 2,4,6,8-壬四烯酸,7-甲基-9-(2,6,6-三甲基-1-环己烯-1-基)-,(2E,4E,6Z,8E)-
• 英文名称: 13-demethyl 9-cis-retinoic acid
• 英文别名: (2E,4E,6Z,8E)-7-methyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
• CAS: 131235-61-5
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: JKGJBNBHOCVZCW-MCKULUFJSA-N

物化性质

• 熔点：
  104-106 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  452.7±14.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 9Z-13-demethylretinoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以73%的产率得到2,4,6,8-壬四烯酸,7-甲基-9-(2,6,6-三甲基-1-环己烯-1-基)-,(2E,4E,6Z,8E)-
  参考文献：
  名称：

  Preparation and biological activity of 13-substituted retinoic acids

  摘要：

  13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.047

文献信息

• STERO CONTROLLED SYNTHESIS OF (E,Z)-DIENALS VIA TANDEM RH(I) CATALYZED PROPARGYL CLAISEN REARRANGEMENT
  申请人：The Florida State University Research Foundation, Inc.

  公开号：US20150361019A1

  公开（公告）日：2015-12-17

  A novel Rh(I)-catalyzed approach to synthesizing functionalized (E,Z) dienal compounds has been developed via tandem transformation where a stereoselective hydrogen transfer follows a propargyl Claisen rearrangement. Z-Stereochemistry of the first double bond suggests the involvement of a six-membered cyclic intermediate whereas the E-stereochemistry of the second double bond stems from the subsequent protodemetallation step giving an (E,Z)-dienal. The reaction may be represented by the following sequence.

  已经开发出一种新颖的Rh(I)催化方法，用于合成功能化的(E,Z)二烯醛化合物，通过串联转化，其中立体选择性的氢转移跟随着一个炔丙基Claisen重排。第一个双键的Z-立体化学表明涉及一个六元环中间体，而第二个双键的E-立体化学源自随后的脱金属化步骤，形成一个(E,Z)-二烯醛。该反应可以用以下序列表示。
• METHODS FOR ENHANCING HEMATOPOIETIC STEM/PROGENITOR CELL ENGRAFTMENT
  申请人：CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：US20150246075A1

  公开（公告）日：2015-09-03

  Described herein are methods for enhancing engraftment of hematopoietic stem and progenitor cells using compounds identified using a zebrafish model of hematopoietic cell engraftment. The compounds can be used to treat hematopoietic stem cells ex vivo prior to transplantation of the cells. Alternatively, the compounds can be administered to an individual undergoing cell transplantation.
• STEREO CONTROLLED SYNTHESIS OF (E,Z)-DIENALS VIA TANDEM RH(I) CATALYZED PROPARGYL CLAISEN REARRANGEMENT
  申请人：The Florida State University Research Foundation, Inc.

  公开号：US20170129865A1

  公开（公告）日：2017-05-11

  A novel Rh(I)-catalyzed approach to synthesizing functionalized (E,Z) dienal compounds has been developed via tandem transformation where a stereoselective hydrogen transfer follows a propargyl Claisen rearrangement. Z-Stereochemistry of the first double bond suggests the involvement of a six-membered cyclic intermediate whereas the E-stereochemistry of the second double bond stems from the subsequent protodemetallation step giving an (E,Z)-dienal. The reaction may be represented by the following sequence.
• US9573871B2
  申请人：——

  公开号：US9573871B2

  公开（公告）日：2017-02-21
• US9758499B2
  申请人：——

  公开号：US9758499B2

  公开（公告）日：2017-09-12