(2Z)-6-(4'-methoxybenzyloxy)-2-hexen-1-ol | 307497-64-9

• 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: (2Z)-6-(4'-methoxybenzyloxy)-2-hexen-1-ol
• CAS: 307497-64-9
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: WLUMDRZGAKRQFU-RQOWECAXSA-N

物化性质

• 沸点：
  365.9±42.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2Z)-6-(4'-methoxybenzyloxy)-2-hexen-1-ol 在 lithium aluminium tetrahydride 、 正丁基锂 、 四溴化碳 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (2E,5Z)-9-(4'-methoxybenzyloxy)-2,5-nonadien-1-ol
  参考文献：
  名称：

  Transformation of cis-Epoxy Compound to cis-2,3-Disubstituted Oxane and Investigation on Propagation Step in the Ring-Expansion Reactions of cis,trans-Diepoxy Systems

  摘要：

  Conversion of cis-epoxy compounds by successive ring-expansion reaction into trans-fused cyclic ethers was examined from both the initiation step and the propagation step. The ring-expansion reaction of cis-4,5-epoxy compounds containing a leaving group on C-1 was attempted as a unit process for the successive reaction. When a chloromesyl group was used as a leaving group, the ring expansion proceeded to give an oxane derivative (endo-type product) preferentially. On the other hand, investigation of the propagation step was carried out with respect to epoxy oxane derivatives. It was clarified that the ring-expansion reaction of cis-2,3-disubstituted oxane derivatives provided spiro acetals as products, not the desired trans-fused cyclic ethers, owing to the reaction pathway triggered by 1,2-hydride rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00622-0
• 作为产物：
  描述：

  6-[(4-methoxyphenyl)methoxy]-2-hexyn-1-ol 在 Lindlar's catalyst 吡啶 、 喹啉 、 氢气 作用下， 反应 1.5h， 以98%的产率得到(2Z)-6-(4'-methoxybenzyloxy)-2-hexen-1-ol
  参考文献：
  名称：

  Transformation of cis-Epoxy Compound to cis-2,3-Disubstituted Oxane and Investigation on Propagation Step in the Ring-Expansion Reactions of cis,trans-Diepoxy Systems

  摘要：

  Conversion of cis-epoxy compounds by successive ring-expansion reaction into trans-fused cyclic ethers was examined from both the initiation step and the propagation step. The ring-expansion reaction of cis-4,5-epoxy compounds containing a leaving group on C-1 was attempted as a unit process for the successive reaction. When a chloromesyl group was used as a leaving group, the ring expansion proceeded to give an oxane derivative (endo-type product) preferentially. On the other hand, investigation of the propagation step was carried out with respect to epoxy oxane derivatives. It was clarified that the ring-expansion reaction of cis-2,3-disubstituted oxane derivatives provided spiro acetals as products, not the desired trans-fused cyclic ethers, owing to the reaction pathway triggered by 1,2-hydride rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00622-0

文献信息

• Total Synthesis of Δ¹²-Prostaglandin J₃: Evolution of Synthetic Strategies to a Streamlined Process
  作者：K. C. Nicolaou、Kiran Kumar Pulukuri、Ruocheng Yu、Stephan Rigol、Philipp Heretsch、Charles I. Grove、Christopher R. H. Hale、Abdelatif ElMarrouni

  DOI：10.1002/chem.201601449

  日期：2016.6.13

  cross‐conjugated dienone structural motif of 1 was forged by an aldol reaction/dehydration sequence from key building blocks enone 13 and aldehyde 14, whose lone stereocenters were generated by an asymmetric Tsuji–Trost reaction and an asymmetric Mukaiyama aldol reaction, respectively. During this program, a substituent‐governed regioselectivity pattern for the Rh‐catalyzed C−H functionalization of cyclopentenes

  Δ的总合成12 -前列腺素Ĵ 3（Δ 12 -PGJ 3，1），所报告的白血病干细胞消融器，通过若干战略和战术进行说明。关键的共轭烯酮13和醛14的醛醇缩合反应/脱水序列伪造了1的标志性交叉共轭二烯酮结构基序。，其单独的立体中心分别由不对称的Tsuji-Trost反应和不对称的Mukaiyama aldol反应产生。在该程序中，发现了用于Rh催化的环戊烯和相关烯烃的CH官能化的取代基控制的区域选择性模式。1的合成从最初的策略发展到最终的简化流程，这是通过改进片段13和14的结构，探索迄今未充分利用的手性内酯合成子57的化学性质以及环戊烯酮中间体的非对映选择性烷基化来进行的。 。所描述的化学设置了大规模生产Δ的阶段12 -PGJ3并设计类似物用于进一步的生物学和药理研究。