(6-chlorohexa-1,2-dien-1-yl)benzene | 56644-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6-chlorohexa-1,2-dien-1-yl)benzene
• 英文别名: 6-Chloro-1-phenyl-1,2-hexadien
• CAS: 56644-02-1
• 化学式: C₁₂H₁₃Cl
• 分子量: 192.688
• InChiKey: RUXWFPMSCBZVMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (6-chlorohexa-1,2-dien-1-yl)benzene 、 丙酮氰醇 在 bis(1,5-cyclooctadiene)nickel (0) 、 (-)-1,2-双((2R,5R)-2,5-二苯基膦)乙烷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 12.0h， 以52%的产率得到(S,E)-5-chloro-2-styrylpentanenitrile
  参考文献：
  名称：

  镍催化的异戊烯不对称氢氰化。

  摘要：

  由（R，R）-Ph-BPE-Ni（0）络合物催化剂催化的丙二烯的第一催化对映选择性氢氰化反应已经完成。以良好的收率和优异的对映选择性（高达98％ee）获得了许多旋光性烯丙基腈。

  DOI：

  10.1021/acs.orglett.9b03938
• 作为产物：
  描述：

  在 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 (6-chlorohexa-1,2-dien-1-yl)benzene
  参考文献：
  名称：

  Mild-Condition Synthesis of Allenes from Alkynes and Aldehydes Mediated by Tetrahydroisoquinoline (THIQ)

  摘要：

  A practical 1,2,3,4-tetrahydroisoquinoline (THIQ)-mediated synthesis of 1,3-disubstituted allenes from terminal alkynes and aldehydes under mild conditions in the presence of CuBr first and then ZnI2 was reported. This telescoped allene synthesis reaction includes three consecutive steps and two reactions: first, a room-temperature CuBr-catalyzed synthesis of propargylamines, exo-yne-THIQs, from terminal alkynes, aldehydes, and THIQ then filtration of the CuBr catalyst, and finally the ZnI2-mediated allene synthesis from the generated exo-yne-THIQs under mild conditions (either at room temperature or heating at 50 or 75 degrees C). A wide range of aliphatic or aromatic aldehydes and terminal alkynes are tolerated, affording the allene products in up to 92% yield. Especially, temperature-sensitive aldehydes can be used in the reaction system. Preliminary exploration of the asymmetric allene synthesis has also been conducted, and a moderate enantioselectivity has been achieved. Finally, the relative reactivities of several secondary amines were compared with THIQ, showing that THIQ is the best of these amines in the synthesis of allenes under mild reaction conditions.

  DOI：

  10.1021/jo4018183

文献信息

• Ligand‐Controlled Regiodivergent Cyanoboration of Internal Allenes by Copper Catalysis
  作者：Hui Hu、Guo‐Cui Ji、Linjuan Jiang、Siwei Bi、Yuan‐Ye Jiang、Yuanhong Liu

  DOI：10.1002/anie.202210338

  日期：2022.12.19

  The first copper-catalyzed regiodivergent cyanoboration of internal allenes with B2pin2 and NCTS derivatives has been developed. MeOH was identified as the necessary additive for the regeneration of LCu-Bpin species. Computational studies revealed that the copper-mediated allylic cyanation is the regio- and stereo-determining step, while the MeOH-assisted transmetalation with B2pin2 is the rate-determining

  已经开发出第一个铜催化的具有 B 2引脚2和 NCTS 衍生物的内部丙二烯区域发散氰基硼化反应。MeOH 被确定为 LCu-Bpin 物种再生的必要添加剂。计算研究表明，铜介导的烯丙基氰化作用是区域和立体决定步骤，而甲醇辅助的 B 2 pin 2金属转移是速率决定步骤。
• Nickel-Catalyzed Asymmetric Hydrocyanation of Allenes
  作者：Jinguo Long、Jihui Gao、Xianjie Fang

  DOI：10.1021/acs.orglett.9b03938

  日期：2020.1.17

  The first catalytic enantioselective hydrocyanation of allenes catalyzed by a (R,R)-Ph-BPE-Ni(0) complex catalyst has been accomplished. Numerous optically active allylic nitriles were obtained in good yield with excellent enantioselectivities (up to 98% ee).

  由（R，R）-Ph-BPE-Ni（0）络合物催化剂催化的丙二烯的第一催化对映选择性氢氰化反应已经完成。以良好的收率和优异的对映选择性（高达98％ee）获得了许多旋光性烯丙基腈。
• Mild-Condition Synthesis of Allenes from Alkynes and Aldehydes Mediated by Tetrahydroisoquinoline (THIQ)
  作者：Guo-Jie Jiang、Qin-Heng Zheng、Meng Dou、Lian-Gang Zhuo、Wei Meng、Zhi-Xiang Yu

  DOI：10.1021/jo4018183

  日期：2013.12.6

  A practical 1,2,3,4-tetrahydroisoquinoline (THIQ)-mediated synthesis of 1,3-disubstituted allenes from terminal alkynes and aldehydes under mild conditions in the presence of CuBr first and then ZnI2 was reported. This telescoped allene synthesis reaction includes three consecutive steps and two reactions: first, a room-temperature CuBr-catalyzed synthesis of propargylamines, exo-yne-THIQs, from terminal alkynes, aldehydes, and THIQ then filtration of the CuBr catalyst, and finally the ZnI2-mediated allene synthesis from the generated exo-yne-THIQs under mild conditions (either at room temperature or heating at 50 or 75 degrees C). A wide range of aliphatic or aromatic aldehydes and terminal alkynes are tolerated, affording the allene products in up to 92% yield. Especially, temperature-sensitive aldehydes can be used in the reaction system. Preliminary exploration of the asymmetric allene synthesis has also been conducted, and a moderate enantioselectivity has been achieved. Finally, the relative reactivities of several secondary amines were compared with THIQ, showing that THIQ is the best of these amines in the synthesis of allenes under mild reaction conditions.