(R)-(-)-2-Methylvalerolactone | 73746-79-9

• 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: (R)-(-)-2-Methylvalerolactone
• 英文别名: (R)-2-methyl-5-pentanolide；(R)-2-methylvalerolactone；(3R)-3-methyloxan-2-one
• CAS: 73746-79-9
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: SPEHEHYVDRYEDX-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  5-羟基-戊腈 在 2,6-二甲基吡啶 、 盐酸 、 乙醇 、 硫酸 、 水 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (R)-(-)-2-Methylvalerolactone
  参考文献：
  名称：

  Asymmetric synthesis of 2-substituted butyrolactones and valerolactones

  摘要：

  DOI：

  10.1021/jo01302a009

文献信息

• Promotion of Asymmetric Aza-Claisen Rearrangement of N-Allylic Carboxamides Using Excess Base
  作者：Tetsuto Tsunoda、Makoto Yoshizuka、Takeshi Nishii、Hiromi Sasaki、Junko Kitakado、Noriko Ishigaki、Shinobu Okugawa、Hiroto Kaku、Mitsuyo Horikawa、Makoto Inai

  DOI：10.1055/s-0031-1289899

  日期：2011.12

  The aza-Claisen rearrangement of the enolate of N-(Z)-crotyl-N-(S)-phenethylpropanamide did not proceed in the presence of 1.5 equivalents of LHMDS as a base. However, the use of a large excess of base (10 equiv) promoted the reaction to give N-(S)-phenethyl-anti-2,3-dimethylpent-4-enamide with good stereoselectivities (anti/syn = ca. 95:5). An excess of base stabilized the amide enolates and prevented the decomposition to the ketene to prompt the rearrangement of various carboxamides with good stereoselectivity. This reaction provided a new method for the construction of asymmetric quaternary carbon centers.

  N-(Z)-烯丙基-N-(S)-苯乙基丙酰胺的烯醇负离子在1.5当量的LHMDS作为碱的存在下并未发生aza-Claisen重排。然而，使用大量的碱（10当量）促进了反应的进行，生成具有良好立体选择性的N-(S)-苯乙基-反-2,3-二甲基戊-4-烯酰胺（反/顺 = 约 95:5）。过量的碱稳定了酰胺烯醇负离子，防止了其分解为烯酮，从而促使各种酰胺进行具有良好立体选择性的重排。这一反应提供了一种构建不对称季碳中心的新方法。
• Enantioselective Synthesis of 2-Substituted 6- and 7-Membered Lactones via α-Alkylation of Lactone Hydrazones
  作者：Dieter Enders、Robert Gröbner、Jan Runsink

  DOI：10.1055/s-1995-4431

  日期：1995.8

  2-Alkyl-substituted lactones 4 were synthesized in good overall yields and high enantiomeric purities (ee=90-94%) by deprotonation and alkylation of the corresponding lactone SAMP-hydrazones 2 and subsequent oxidative cleavage of the product hydrazones 3 by ozonolysis. The lactone hydrazones 2, in turn, were prepared in good yields by silver promoted cyclization of ω-chloroalkanohydrazides 1.

  通过相应内酯 SAMP-腙 2 的去质子化和烷基化以及随后通过臭氧分解对产物腙 3 进行氧化裂解，以良好的总产率和高对映体纯度 (ee=90-94%) 合成 2-烷基取代的内酯 4。反过来，通过银促进β-氯代烷酰肼 1 的环化，以良好的收率制备了内酯腙 2。
• Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides
  作者：Kevin S. Orwig、Thomas A. Dix

  DOI：10.1016/j.tetlet.2005.08.056

  日期：2005.10

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.
• Ozegowski, Ruediger; Kunath, Annamarie; Schick, Hans, Liebigs Annalen der Chemie, 1994, # 10, p. 1019 - 1024
  作者：Ozegowski, Ruediger、Kunath, Annamarie、Schick, Hans

  DOI：——

  日期：——
• CRYSTALLINE FORM OF A MDM2 INHIBITOR
  申请人：AMGEN INC.

  公开号：EP3008039B1

  公开（公告）日：2020-11-11