(4RS)-2-Methyl-4-phenylpent-1-en-3-one | 252201-49-3

• 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: (4RS)-2-Methyl-4-phenylpent-1-en-3-one
• 英文别名: 2-methyl-4-phenyl-1-penten-3-one；2-Methyl-4-phenylpent-1-en-3-one；2-methyl-4-phenylpent-1-en-3-one
• CAS: 252201-49-3
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: VDMLYWBCJBXDDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4RS)-2-Methyl-4-phenylpent-1-en-3-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (3RS,4RS)-2-methyl-4-phenylpent-1-en-3-ol 、 (3RS,4SR)-2-methyl-4-phenylpent-1-en-3-ol
  参考文献：
  名称：

  Substrate-Directed Diastereoselective Hydroformylation: Key Step for the Assembly of Polypropionate Subunits

  摘要：

  Stereoselective hydroformylation of methallylic alcohols of types 3 and 4, that employed the substrate-bound catalyst-directing ortho-diphenyl-phosphanylbenzoyl (o-DPPB) group, was used as a key step for the construction of bifunctionalized stereotriads, which ale central building blocks of polyketide natural products. The required diastereomerically pure syn- and anti- starting methallylic alcohol systems 3 and 4 were obtained either by Cram-selective carbonyl reduction, Frater alkylation, or by chelation-controlled carbonyl reduction. Enantiomerically pure stereotriad building blocks were derived from a combination of an Evans aldol addition and subsequent o-DPPB-directed stereoselective hydroformylation (-->24). A crystal structure analysis for steretriad building block 24 confirmed the relative and absolute configuration of the stereogenic centers. Additionally, it provided evidence for a previously postulated preferred conformation of the catalyst-directing o-DPPB group as well as of the polyketide main chain.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2819::aid-chem2819>3.0.co;2-z
• 作为产物：
  描述：

  2-Methyl-4-phenylpent-1-en-3-ol 在 aluminum oxide 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以99%的产率得到(4RS)-2-Methyl-4-phenylpent-1-en-3-one
  参考文献：
  名称：

  Substrate-Directed Diastereoselective Hydroformylation: Key Step for the Assembly of Polypropionate Subunits

  摘要：

  Stereoselective hydroformylation of methallylic alcohols of types 3 and 4, that employed the substrate-bound catalyst-directing ortho-diphenyl-phosphanylbenzoyl (o-DPPB) group, was used as a key step for the construction of bifunctionalized stereotriads, which ale central building blocks of polyketide natural products. The required diastereomerically pure syn- and anti- starting methallylic alcohol systems 3 and 4 were obtained either by Cram-selective carbonyl reduction, Frater alkylation, or by chelation-controlled carbonyl reduction. Enantiomerically pure stereotriad building blocks were derived from a combination of an Evans aldol addition and subsequent o-DPPB-directed stereoselective hydroformylation (-->24). A crystal structure analysis for steretriad building block 24 confirmed the relative and absolute configuration of the stereogenic centers. Additionally, it provided evidence for a previously postulated preferred conformation of the catalyst-directing o-DPPB group as well as of the polyketide main chain.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2819::aid-chem2819>3.0.co;2-z

文献信息

• Vinyl Ketones to Allenes:  Preparation of 1,3-Dien-2-yl Triflates and Their Application in Pd-Catalyzed Reactions with Soft Nucleophiles
  作者：Masamichi Ogasawara、Yonghui Ge、Koichi Uetake、Tamotsu Takahashi

  DOI：10.1021/ol052426u

  日期：2005.12.1

  [chemical reaction: see text]. A general route of converting alkenyl ketones to functionalized allenes was developed. Substituted 1,3-dien-2-yl triflates, which were prepared from the alkenyl ketones via silyl dienol ethers, were excellent substrates for the palladium-catalyzed reaction with soft nucleophiles giving the multisubstituted allenes in high yields. Comparison between the dienyl triflates and

  [化学反应：见正文]。开发了将烯基酮转化为官能化的烯的一般路线。由烯基酮经甲硅烷基二烯醇醚制备的1,3-二烯-2-基三氟甲磺酸酯是钯与软亲核试剂催化反应的极佳底物，可高收率得到多取代的烯。还研究了在Pd催化的反应中二烯基三氟甲磺酸酯和类似溴代亚胺之间的比较。
• Substrate-Directed Diastereoselective Hydroformylation: Key Step for the Assembly of Polypropionate Subunits
  作者：Bernhard Breit、Mario Dauber、Klaus Harms

  DOI：10.1002/(sici)1521-3765(19991001)5:10<2819::aid-chem2819>3.0.co;2-z

  日期：1999.10.1

  Stereoselective hydroformylation of methallylic alcohols of types 3 and 4, that employed the substrate-bound catalyst-directing ortho-diphenyl-phosphanylbenzoyl (o-DPPB) group, was used as a key step for the construction of bifunctionalized stereotriads, which ale central building blocks of polyketide natural products. The required diastereomerically pure syn- and anti- starting methallylic alcohol systems 3 and 4 were obtained either by Cram-selective carbonyl reduction, Frater alkylation, or by chelation-controlled carbonyl reduction. Enantiomerically pure stereotriad building blocks were derived from a combination of an Evans aldol addition and subsequent o-DPPB-directed stereoselective hydroformylation (-->24). A crystal structure analysis for steretriad building block 24 confirmed the relative and absolute configuration of the stereogenic centers. Additionally, it provided evidence for a previously postulated preferred conformation of the catalyst-directing o-DPPB group as well as of the polyketide main chain.