trans-p-menthanolide | 38049-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: trans-p-menthanolide
• 英文别名: (+)-(1R,3R,4S)-3,9-epoxy-p-mentha-8(10)-en-9-one；(3aS,6R,7aR)-6-methyl-3-methylene-3a,4,5,6,7,7a-hexahydrobenzofuran-2-one；(3R,4R)-3,9-oxa-9-oxo-8(10)-p-menthene；(+)-(3aS,6R,7aR)-hexahydro-6-methyl-3-methylenebenzofuran-2(3H)-one；(3aS,6R,7aR)-6-methyl-3-methylidene-3a,4,5,6,7,7a-hexahydro-1-benzofuran-2-one
• CAS: 38049-03-5
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: NWXGMAMXYQGHII-BWVDBABLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-p-menthanolide 在 Rh(H)(PEt₃)₃ 作用下， 反应 20.0h， 以92%的产率得到(6R)-3,6-dimethyl-5,6,7,7a-tetrahydro-2(4H)-benzofuranone
  参考文献：
  名称：

  Enzyme-Mediated Preparation of Enantiomerically Pure p-Menthan- 3,9-diols and Their Use for the Synthesis of Natural p-Menthane Lactones and Ethers

  摘要：

  The diasiereoselective preparation of the p-menthane-3,9-diols (+/-)-12, (+/-)-13a, (+/-)-13b, and (+/-)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

  DOI：

  10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9
• 作为产物：
  描述：

  (+)-(1R,3R,4S)-p-menth-8(10)-ene-3,9-diol diacetate 在 manganese(IV) oxide 、 氢氧化钾 、 copper(II) sulfate 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 trans-p-menthanolide
  参考文献：
  名称：

  Enzyme-Mediated Preparation of Enantiomerically Pure p-Menthan- 3,9-diols and Their Use for the Synthesis of Natural p-Menthane Lactones and Ethers

  摘要：

  The diasiereoselective preparation of the p-menthane-3,9-diols (+/-)-12, (+/-)-13a, (+/-)-13b, and (+/-)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

  DOI：

  10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9

文献信息

• Stereoselective synthesis and application of isopulegol-based bi- and trifunctional chiral compounds
  作者：Tam Minh Le、Thu Huynh、Gábor Endre、András Szekeres、Ferenc Fülöp、Zsolt Szakonyi

  DOI：10.1039/d0ra07739a

  日期：——

  was subjected to hydroxylation and epoxidation, then aminolysis of the served oxiranes delivered aminodiols. On the other hand, (−)-isopulegol was oxidised to diol, which was again converted into both dibenzyl- and monobenzyl-protected diol derivatives. The products were transformed into aminoalcohols and aminodiols, respectively, by aminolysis of their epoxides. The ring opening of epoxides, derived

  从市售的 (-)-isopulegol 开发了一个新的基于异胡薄荷醇的双功能和三功能手性配体家族。实现了伯胺对 (+)-α-亚甲基-γ-丁内酯的亲核加成，然后还原获得的 β-氨基内酯，在高度立体选择性反应中提供氨基二醇。(-)-异胡薄荷醇的环氧化和随后用伯胺开环的环氧乙烷产生N-取代的氨基二醇。还研究了这些氨基二醇与甲醛的区域选择性闭环。异胡薄荷醇的苄基化提供O-苄基保护的异胡薄荷醇，其通过以下途径转化为氨基醇相应环氧化物的环氧化和开环。首先对苄基保护的异胡薄荷醇进行羟基化和环氧化，然后对所提供的环氧乙烷进行氨解，从而产生氨基二醇。另一方面，(-)-异胡薄荷醇被氧化为二醇，其再次转化为二苄基和单苄基保护的二醇衍生物。通过环氧化物的氨解作用，产物分别转化为氨基醇和氨基二醇。衍生自二醇与伯胺的环氧化物的开环也用于产生氨基三醇。(-)-异胡薄荷醇或其衍生物与 OsO 4的二羟基化/NMO 得到基
• Isopulegol as a Model Compound: Metalation and Substitution of an Allylic Position in the Presence of an Unprotected Hydroxy Function
  作者：Manfred Schlosser、Martina Kotthaus

  DOI：10.1002/(sici)1099-0690(199902)1999:2<459::aid-ejoc459>3.0.co;2-f

  日期：1999.2
• Nishitani, Kiyoshi; Fukuda, Hiroshi; Yamakawa, Koji, Heterocycles, 1992, vol. 33, # 1, p. 97 - 100
  作者：Nishitani, Kiyoshi、Fukuda, Hiroshi、Yamakawa, Koji

  DOI：——

  日期：——
• A Short Route to (−)-Mintlactone by Thallium(III)-Mediated Cyclization of (−)-Isopulegol
  作者：Helena M. C. Ferraz、Mônica V. A. Grazini、Carlos M. R. Ribeiro、Ursula Brocksom、Timothy J. Brocksom

  DOI：10.1021/jo991802j

  日期：2000.4.1
• Brocksom, Timothy J.; Santos, Reginaldo B. dos; Varanda, Newton A., Synthetic Communications, 1988, vol. 18, # 12, p. 1403 - 1410
  作者：Brocksom, Timothy J.、Santos, Reginaldo B. dos、Varanda, Newton A.、Brocksom, Ursula

  DOI：——

  日期：——