(Z)-1-Cyclopropyl-1-hexen | 148311-91-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (Z)-1-Cyclopropyl-1-hexen
• 英文别名: cis-1-Hexenyl-cyclopropane；[(Z)-hex-1-enyl]cyclopropane
• CAS: 148311-91-5
• 化学式: C₉H₁₆
• 分子量: 124.226
• InChiKey: QAMUELDWLSZYFW-WAYWQWQTSA-N

物化性质

• 沸点：
  147.5±7.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)
• 保留指数：
  922.6;923.9

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (Z)-1-bromohex-1-ene 、 3-溴丙炔 在 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydroxide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 以68%的产率得到(Z)-1-Cyclopropyl-1-hexen
  参考文献：
  名称：

  Aryl and vinyl cyclopropanes through the in situ generation of B-cyclopropyl-9-BBN and its Suzuki–Miyaura coupling

  摘要：

  Dihydroboration of propargyl bromide with 9-BBN-H followed by treatment of the adduct with aqueous sodium hydroxide affords the hydroxy(cyclopropyl)borate complex (1), which undergoes efficient palladium-catalyzed cross-coupling to produce a variety of aryl and vinyl cyclopropanes (2) in good to excellent yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00605-5

文献信息

• Pheromone 69.¹Stereoselektive Synthesen nichtkonjugierter bisolefinischer Lepidopteren-Pheromone und Strukturanaloger
  作者：Hans Jürgen Bestmann、Thomas Zeibig、Otto Vostrowsky

  DOI：10.1055/s-1990-27089

  日期：——

  Pheromones 69.1 Stereoselective Syntheses of Nonconjugated Bisolefinic Lepidoptera Pheromones and Structural Analogs Coupling reactions of lithium compounds, (Z)-carbonyl olefination of phosphonium ylides and "crossed" Wittig olefination of bisylides are the key reaction steps in the synthesis principle for nonconjugated, bisolefinic Lepidoptera pheromones and structural analogs. Double unsaturated (E,Z)- and (E,E)-1-vinyl halides are converted into the corresponding (E,Z)- and (E,E)-1-vinyl lithium compounds and coupled selectively to (E,Z)- and (E,E)-alkadienols, alkadienals and alkadienyl acetates with different carbon chain length, geometry and relative positions of double bonds. "Crossed" Wittig reactions of 1,ω-alkylidene bisylides with two different alkanals gives rise to the formation of corresponding (Z,Z)-dienic sex attractants and derivatives. A monounsaturated (E)-1-vinyl iodide is the synthon for the preparation of an (E)-alkenyl bromide which is converted to an (E)-alkenyl phosphonium salt and (Z)-selectively olefinated to (Z,E)-isomers of moth sex pheromones.

  信息素 69.1 非共轭双烯类鳞翅目昆虫信息素及其结构类似物的立体选择性合成 锂化合物的偶联反应、磷烷阳离子盐的(Z)-羰基烯化以及双阳离子的“交叉”维蒂格烯化是合成非共轭双烯类鳞翅目昆虫信息素及其结构类似物的关键反应步骤。双不饱和的(E,Z)-和(E,E)-1-烯基卤化物转化为相应的(E,Z)-和(E,E)-1-烯基锂化合物，然后选择性偶联生成不同碳链长度、几何结构及双键相对位置的(E,Z)-和(E,E)-烷二醇、烷二醛及烷二烯基醋酸酯。1,ω-烷基烯基双阳离子与两种不同烷基醛的“交叉”维蒂格反应生成相应的(Z,Z)-二烯性别吸引剂及其衍生物。单不饱和的(E)-1-烯基碘化物是制备(E)-烯基溴化物的合成子，后者转化为(E)-烯基磷烷盐，并选择性地烯化为蛾类性别信息素的(Z,E)-异构体。
• BESTMANN, HANS JURGEN;ZEIBIG, THOMAS;VOSTROWSKY, OTTO, SYNTHESIS,(1990) N1, C. 1039-1047
  作者：BESTMANN, HANS JURGEN、ZEIBIG, THOMAS、VOSTROWSKY, OTTO

  DOI：——

  日期：——
• Aryl and vinyl cyclopropanes through the in situ generation of B-cyclopropyl-9-BBN and its Suzuki–Miyaura coupling
  作者：John A. Soderquist、Ramon Huertas、Gisela Leon-Colon

  DOI：10.1016/s0040-4039(00)00605-5

  日期：2000.6

  Dihydroboration of propargyl bromide with 9-BBN-H followed by treatment of the adduct with aqueous sodium hydroxide affords the hydroxy(cyclopropyl)borate complex (1), which undergoes efficient palladium-catalyzed cross-coupling to produce a variety of aryl and vinyl cyclopropanes (2) in good to excellent yields. (C) 2000 Elsevier Science Ltd. All rights reserved.