(4S)-2-Methyl-8-phenyl-5-octyn-4-ol | 627526-51-6

• 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: (4S)-2-Methyl-8-phenyl-5-octyn-4-ol
• 英文别名: (4S)-2-methyl-8-phenyloct-5-yn-4-ol
• CAS: 627526-51-6
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: LDPHTYFEEVZHJS-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (4S)-2-Methyl-8-phenyl-5-octyn-4-ol 在 palladium dichloride copper dichloride 作用下， 以 四氢呋喃 为溶剂， 30.0 ℃ 、2.03 MPa 条件下， 反应 4.0h， 生成 (S)-(Z)-α-(1-chloro-3-phenylpropylidene)-β-(i-butyl)-β-lactone 、 (R)-(Z)-α-(1-chloro-3-phenylpropylidene)-β-isobutyl-β-lactone
  参考文献：
  名称：

  Mild and Efficient Synthesis of (Z)-α-Chloroalkylidene-β-lactones via the PdCl₂-Catalyzed Cyclocarbonylation of 2-Alkynols

  摘要：

  A mild and efficient methodology involving PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 for the synthesis of (Z)-alpha-chloroalkylidene-beta-lactones was developed. Using the readily available optically active propargylic alcohols allows convenient synthesis of the corresponding (Z)-alpha-chloroalkylidene-beta-lactones with high ee values. cis-Chloropalladation was observed as the major pathway, which is unique as compared to the reported data.

  DOI：

  10.1021/ol0357245
• 作为产物：
  描述：

  4-苯基-1-丁炔 、 异戊醛 在 indium(III) bromide 、 S-1,1'-联-2-萘酚 、 N-甲基二环己基胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.42h， 以46%的产率得到(4S)-2-Methyl-8-phenyl-5-octyn-4-ol
  参考文献：
  名称：

  CATALYTIC ENANTIOSELECTIVE ADDITION OF TERMINAL ALKYNES TO ALDEHYDES: PREPARATION OF (S)-(-)-1,3-DIPHENYL-2-PROPYN-1-OL AND (S)-(-)-4-METHYL-1-PHENYL-2-PENTYN-1,4-DIOL

  摘要：

  DOI：

  10.15227/orgsyn.085.0118

文献信息

• Studies on Pd(II)-Catalyzed Synthesis of (<i>Z</i>)-α-Haloalkylidene-β-lactones from Cyclocarbonylation of 2-Alkynols and the Subsequent Coupling Reactions
  作者：Shengming Ma、Bin Wu、Xuefeng Jiang、Shimin Zhao

  DOI：10.1021/jo0480038

  日期：2005.4.1

  A good regio- and stereoselectivity was observed for the PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 affording (Z)-alpha-chloroalkylidene-beta-lactons. The highly optically active (Z)-alpha-chloroalkylidene-beta-lactones could be easily prepared from the readily available optically active propargylic alcohols. The Pd(II)-catalyzed cyclocarbonylation of 2-alkynols with CuBr2 was also studied. Although the yields of (Z)-alpha-bromoalkylidene-beta-lactones were low, due to the relatively higher activity of the C-Br bond, the coupling reactions of (Z)-alpha-bromoalkylidene-beta-lactones were quite smooth to afford the corresponding products in high yields. A rationale for this reaction is discussed.
• CATALYTIC ENANTIOSELECTIVE ADDITION OF TERMINAL ALKYNES TO ALDEHYDES: PREPARATION OF (S)-(-)-1,3-DIPHENYL-2-PROPYN-1-OL AND (S)-(-)-4-METHYL-1-PHENYL-2-PENTYN-1,4-DIOL
  作者：Takita, Ryo、Harada, Shinji、Ohshima, Takashi、Matsunaga, Shigeki、Shibasaki, Masakatsu、Fontaine, Shaun、Robinson, Julia、Danheiser, Rick L.

  DOI：10.15227/orgsyn.085.0118

  日期：——
• Mild and Efficient Synthesis of (<i>Z</i>)-α-Chloroalkylidene-β-lactones via the PdCl₂-Catalyzed Cyclocarbonylation of 2-Alkynols
  作者：Shengming Ma、Bin Wu、Shimin Zhao

  DOI：10.1021/ol0357245

  日期：2003.11.1

  A mild and efficient methodology involving PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 for the synthesis of (Z)-alpha-chloroalkylidene-beta-lactones was developed. Using the readily available optically active propargylic alcohols allows convenient synthesis of the corresponding (Z)-alpha-chloroalkylidene-beta-lactones with high ee values. cis-Chloropalladation was observed as the major pathway, which is unique as compared to the reported data.