(-)-(S)-4-hexyl-4,5-dihydrofuran-2(3H)-one | 123975-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (-)-(S)-4-hexyl-4,5-dihydrofuran-2(3H)-one
• 英文别名: (S)-dihydro-4-hexyl-2(3H)-furanone；(4S)-4-hexyloxolan-2-one
• CAS: 123975-94-0
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: BAKYERABTYQIGZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E,2S,3R)-2-(dibenzylamino)-1-phenylundec-4-en-3-ol 在 甲醇 、 sodium tetrahydroborate 、 臭氧 、 丙酸 、 乙酰氯 作用下， 以 甲苯 为溶剂， 反应 23.5h， 生成 (-)-(S)-4-hexyl-4,5-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  (S)-2-(Dibenzylamino)-3-phenylpropanal as a chiral auxiliary: a new strategy for the asymmetric synthesis of 2-substituted alcohols

  摘要：

  The high levels of 1,2-stereocontrol observed in nucleophilic additions to (S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from L-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along with the (S)-2-(dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols bearing oxygen-or carbon-based 2-substituents. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00120-7

文献信息

• Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues
  作者：Masashi Kawasaki、Daiki Kato、Takuya Okada、Yuko Morita、Yasuo Tanaka、Naoki Toyooka

  DOI：10.1016/j.tet.2020.130984

  日期：2020.3

  β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl

  合成了具有光学活性的β-烷基取代的γ-内酯和威士忌内酯类似物，并评估了其气味特性。在手性中间体的制备过程中，我们发现了3-芳基甲基-2-甲基-1-丙醇的高度对映选择性酯化反应的良好反应条件，以动力学方式将它们拆分。合成内酯的嗅觉评价结果表明，γ-内酯环上的烷基对气味分布起重要作用。
• Kosugi, Hiroshi; Tagami, Katsuya; Takahashi, Akira, Journal of the Chemical Society. Perkin transactions I, 1989, p. 935 - 943
  作者：Kosugi, Hiroshi、Tagami, Katsuya、Takahashi, Akira、Kanna, Hiroshi、Uda, Hisashi

  DOI：——

  日期：——
• KOSUGI, HIROSHI;TAGAMI, KATSUYA;TAKAHASHI, AKIRA;KANNA, HIROSHI;UDA, HISA+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 935-943
  作者：KOSUGI, HIROSHI、TAGAMI, KATSUYA、TAKAHASHI, AKIRA、KANNA, HIROSHI、UDA, HISA+

  DOI：——

  日期：——
• (S)-2-(Dibenzylamino)-3-phenylpropanal as a chiral auxiliary: a new strategy for the asymmetric synthesis of 2-substituted alcohols
  作者：Jonathan Clayden、Catherine McCarthy、John G Cumming

  DOI：10.1016/s0957-4166(98)00120-7

  日期：1998.4

  The high levels of 1,2-stereocontrol observed in nucleophilic additions to (S)-2-(dibenzylamino)-3-phenylpropanal (available in three high-yielding steps from L-phenylalanine) can be converted to remote 1,4-stereocontrol by a stereospecific rearrangement if the nucleophile is a vinyl anion equivalent. Ozonolysis of the product followed by reductive work-up returns an enantiomerically pure 2-substituted alcohol, along with the (S)-2-(dibenzylamino)-3-phenylpropan-1-ol precursor to the starting aldehyde, which functions as a chiral auxiliary. The sequence provides a new strategy for the use of aldehydes as chiral auxiliaries in the synthesis of chiral alcohols bearing oxygen-or carbon-based 2-substituents. (C) 1998 Elsevier Science Ltd. All rights reserved.