4-ethynyl-1-methylcyclohexene | 31929-13-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 4-ethynyl-1-methylcyclohexene
• 英文别名: 1-methyl-4-acetylcyclohexene；4-Aethinyl-1-methyl-cyclohex-1-en；4-Methyl-3-cyclohexenylacetylene
• CAS: 31929-13-2
• 化学式: C₉H₁₂
• 分子量: 120.194
• InChiKey: BGKWGCGASCMSJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  梨醇酯 、 4-ethynyl-1-methylcyclohexene 生成 (E)‐α‐bisabolene
  参考文献：
  名称：

  Termite Trail Attractants: New Syntheses of Racemic (E)-α-, (Z)-α- andβ-Bisabolenes

  摘要：

  Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.

  DOI：

  10.1080/00397919408010239
• 作为产物：
  描述：

  4-甲基环己-3-烯-1-羧酸 在 lithium aluminium tetrahydride 、 甲基锂 、 三苯基膦 、 pyridinium chlorochromate 、 锌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 179.5h， 生成 4-ethynyl-1-methylcyclohexene
  参考文献：
  名称：

  Termite Trail Attractants: New Syntheses of Racemic (E)-α-, (Z)-α- andβ-Bisabolenes

  摘要：

  Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.

  DOI：

  10.1080/00397919408010239

文献信息

• Cyclohexyl- and cyclohexenyl-substituted liquid crystals with low birefringence
  申请人：Displaytech, Inc.

  公开号：US06413448B1

  公开（公告）日：2002-07-02

  A liquid crystal composition comprising a host material and a low birefringence liquid crystal composition of the formula: R1—Ar—R2 wherein R1 and R2, independently of one another, are selected from the group consisting of internally branched alkyl groups having from 4 to 20 carbon atoms, terminally branched alkyl groups having from 3 to 20 carbon atoms, internally branched alkenyl groups having from 3 to 20 carbon atoms and terminally branched alkenyl groups having from 4 to 20 carbon atoms, wherein one or more —CH2— groups in R1 and R2 may be independently replaced with O, said R1 or R2, independently of one another, can be partially or fully halogenated, and wherein one or both of said R1 and R2 can be absent; Ar is a ring core moiety of the general formula: wherein Cyc is a cyclohexyl ring or a cyclohexenyl ring; RX is a phenyl ring which may be optionally substituted with one or more fluorines; RY is a cyclohexyl or cyclohexenyl ring; wherein x and y are 1 and z is 0; wherein A is COO; and B is selected from the group of small alkyl or alkenyl group having from 1 to 8 carbon atoms, COO and OCO; wherein a and b are 1 and d is zero.

  一种液晶组合物，包括宿主材料和低双折射液晶组合物，其化学式为：R1—Ar—R2，其中R1和R2独立地选自以下组中的一种：内部支链烷基，碳数为4到20；末端支链烷基，碳数为3到20；内部支链烯基，碳数为3到20；末端支链烯基，碳数为4到20；其中R1和R2中的一个或多个—CH2—基团可以独立地被O取代，R1或R2中的一个或两个可以部分或完全卤代，其中R1和R2中的一个或两个可以不存在；Ar是一个环核心基团，通式为：其中Cyc是一个环己基环或环己烯基环；RX是苯环，可以选择性地被一个或多个氟取代；RY是环己基或环己烯基环；其中x和y为1，z为0；其中A为COO；B选自具有1到8个碳原子的小烷基或烯基组，COO和OCO之一；其中a和b为1，d为零。
• Catalyzed cycloaddition reactions of α-silyloxy-α,β-unsaturated ketone and aldehyde
  作者：Tadashi Sasaki、Yukio Ishibashi、Masatomi Ohno

  DOI：10.1016/s0040-4039(00)87192-0

  日期：1982.1
• Transformation of nitrimines to acetylenes and allenes. 1,3 Rearrangement of N-nitroenamines to C-nitro compounds
  作者：George Buechi、Hans Wuest

  DOI：10.1021/jo01337a021

  日期：1979.11
• BUECHI G.; WUEEST H., J. ORG. CHEM., 1979, 44, NO 23, 4116-4120
  作者：BUECHI G.、 WUEEST H.

  DOI：——

  日期：——
• Termite Trail Attractants: New Syntheses of Racemic (<i>E</i>)-<i>α</i>-, (<i>Z</i>)-<i>α</i>- and<i>β</i>-Bisabolenes
  作者：Laura Argenti、Fabio Bellina、Adriano Carpita、Nicola Dell'Amico、Renzo Rossi

  DOI：10.1080/00397919408010239

  日期：1994.12

  Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.