5-methyl-1-phenyl-1-hexyn-3-ol | 627526-44-7

• 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: 5-methyl-1-phenyl-1-hexyn-3-ol
• 英文别名: (3S)-5-Methyl-1-phenyl-1-hexyn-3-ol；(3S)-5-methyl-1-phenylhex-1-yn-3-ol
• CAS: 627526-44-7
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: JDZJGOREBVGUNA-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  5-methyl-1-phenyl-1-hexyn-3-ol 在 sodium hydride 、 platinum(II) chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 26.5h， 生成 (1R,6R,7R)-4-isobutyl-7-methyl-6-phenyl-3-oxabicyclo[4.1.0]hept-4-ene 、
  参考文献：
  名称：

  Highly Enantiospecific Platinum-Catalyzed Cycloisomerizations: Synthesis of Enantioenriched Oxabicycloheptene Derivatives

  摘要：

  Enantiospecific cycloisomerizations of 1,6-enynes to form oxabicyclo[4.1.0]heptene derivatives are described. Enantiospecificity is consistently high regardless of alkene or alkyne substitution, providing a general approach to greatly enantioenriched cyclopropanes. Additionally, a model for stereochemical transfer is proposed.

  DOI：

  10.1021/ol400625f
• 作为产物：
  描述：

  5-methyl-1-phenylhex-1-yn-3-one 在 Noyori's catalyst 作用下， 以 异丙醇 为溶剂， 以37%的产率得到5-methyl-1-phenyl-1-hexyn-3-ol
  参考文献：
  名称：

  Highly Enantiospecific Platinum-Catalyzed Cycloisomerizations: Synthesis of Enantioenriched Oxabicycloheptene Derivatives

  摘要：

  Enantiospecific cycloisomerizations of 1,6-enynes to form oxabicyclo[4.1.0]heptene derivatives are described. Enantiospecificity is consistently high regardless of alkene or alkyne substitution, providing a general approach to greatly enantioenriched cyclopropanes. Additionally, a model for stereochemical transfer is proposed.

  DOI：

  10.1021/ol400625f

文献信息

• Chiral Macrocycle-Catalyzed Highly Enantioselective Phenylacetylene Addition to Aliphatic and Vinyl Aldehydes
  作者：Zi-Bo Li、Tian-Dong Liu、Lin Pu

  DOI：10.1021/jo070091j

  日期：2007.6.1

  The 1,1‘-binaphthyl macrocycle (S)-2 is found to be an excellent catalyst for the alkyne addition to aldehydes. In the presence of (S)-2 (20 mol %) and Me2Zn (2 equiv) in THF at room temperature, the addition of phenylacetylene to linear or branched aliphatic aldehydes and vinyl aldehydes gave various propargylic alcohols with 89−96% ee.

  发现1,1'-联萘大环（S）-2是炔烃加成醛的极佳催化剂。在室温下，在THF中存在（S）-2（20 mol％）和Me 2 Zn（2当量）的情况下，将苯乙炔添加到直链或支链脂族醛和乙烯基醛中，制得89-96％的各种炔丙醇ee。
• Enantioselective addition of phenylacetylene to aldehydes catalyzed by polymer-supported titanium(IV) complexes of β-hydroxy amides
  作者：Xin-Ping Hui、Lu-Ning Huang、Ya-Min Li、Ren-Lin Wang、Peng-Fei Xu

  DOI：10.1002/chir.20749

  日期：——

  A series of polymer‐supported chiral β‐hydroxy amides and C2‐symmetric β‐hydroxy amides have been synthesized and successfully used for the enantioselective addition of phenylacetylene to aldehydes. High yields (up to 93%) and enantioselectivities (up to 92% ee) were achieved by using polymer‐supported chiral β‐hydroxy amide 4b. The resin 4b is reused four times, giving the product with enantioselectivity

  合成了一系列聚合物支撑的手性β-羟基酰胺和C 2-对称β-羟基酰胺，并成功用于苯乙炔对醛的对映选择性加成。通过使用聚合物负载的手性β-羟基酰胺4b可以实现高收率（高达93％）和对映选择性（高达92％ee）。树脂4b重复使用四次，得到对映选择性为80％ee的产物。幸运的是，发现该杂多体系不仅适用于芳族醛，而且适用于脂族醛。《手性》，2010年。©2009 Wiley-Liss，Inc.。
• 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：——
• Synthesis of new Schiff base-camphorsulfonyl amide ligands and in situ screening in the asymmetric additions of organozinc reagents to aldehydes
  作者：Jiangtao Sun、Xu Pan、Zhenya Dai、Chengjian Zhu

  DOI：10.1016/j.tetasy.2008.10.017

  日期：2008.11

  We have designed and synthesized a new library of highly modular Schiff base-camphorsulfonyl amide ligands from readily available starting materials. These ligands have been used in the asymmetric addition of diethyl zinc to aldehydes in good yields (up to 91%) and high enantioselectivities (up to 93%). Moreover, when the ligands were used in the asymmetric addition of phenylacetylene to aldehydes, good yields and moderate to high ee values (up to 90%) were obtained. The introduction of the camphorsulfonyl moiety into the ligands is highly critical for the selectivities of the reactions. Published by Elsevier Ltd.