trans-sabinene hydrate | 7712-82-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: trans-sabinene hydrate
• 英文别名: sabinene hydrate；(+)-trans-Sabinenhydrat；(1S,2S,5R)-2-methyl-5-propan-2-ylbicyclo[3.1.0]hexan-2-ol
• CAS: 7712-82-5
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: KXSDPILWMGFJMM-KXUCPTDWSA-N

物化性质

• 沸点：
  201.7±8.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  trans-sabinene hydrate 在 potassium permanganate 作用下， 生成 (1S,4S)-thujane-4,7-diol
  参考文献：
  名称：

  Sabinene Hydrate: a Constituent of American Peppermint Oil¹

  摘要：

  DOI：

  10.1021/ja01556a042
• 作为产物：
  描述：

  乙酸桧酯 在 铂 氨 、 氢气 、 氧气 、 sodium 、 孟加拉红内酯 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 trans-sabinene hydrate
  参考文献：
  名称：

  金钟柏的绝对配置

  摘要：

  （+）-顺式-和（+）-反-金钟柏（XIV和XV）已通过（+）-pulegene（XIII）与（+）-pulegone（IX）相关。使用立体定向反应，金钟柏系列的烃已与它们的氧化成员相连。Norin对这些物质发现的绝对构型与我们的发现相符。

  DOI：

  10.1016/0040-4020(66)80132-1

文献信息

• Zur Kenntnis ätherischer Öle. 1. Mitteilung. Zur Kenntnis des Mandarinenschalen-Öls (<i>Citrus reticulata</i>B<scp>LANCO</scp>, bzw.<i>Citrus nobilis var. deliciosa</i>S<scp>WINGLE</scp>„Mandarin”︁)
  作者：E. Kugler、E. sz. Kováts

  DOI：10.1002/hlca.19630460506

  日期：——

  The volatile part of the essential oil of mandarine peel has been analysed. The crude, pressed oil was first divided into various fractions, mainly with the aid of physical methods. On distillation of these fractions the pure components could be isolated by preparative gas chromatography.

  分析了柑桔皮精油的挥发性部分。首先，借助于物理方法，首先将粗制的压制油分为不同的馏分。在蒸馏这些馏分时，可以通过制备气相色谱法分离纯组分。
• Total synthesis of dl-trans-sabinene hydrate, and related monterpenes
  作者：Wayne I. Fanta、William F. Erman

  DOI：10.1021/jo01268a081

  日期：1968.4
• A convenient synthesis of trans-sabinene hydrate from (−)-3-thujol via a highly selective ene reaction of singlet oxygen
  作者：Peter Baeckström、Bohumir Koutek、David Šaman、Jan Vrkoč

  DOI：10.1016/0968-0896(96)00020-x

  日期：1996.3

  trans-Sabinene hydrate (1), was synthesized from (-)-3-thujol (2) in four steps. The key step was the selective formation of trans-2-hydroxy-3-thujene (6) by photooxygenation of a 3:1 mixture of 2- and 3-thujenes (4 and 5) obtained from (-)-3-thujol mesylate (3). Hydrogenation of 6 gave compound 1 in 46% overall yield. Copyright (C) 1996 Elsevier Science Ltd
• Stereochemical mechanism of two sabinene hydrate synthases forming antipodal monoterpenes in thyme (Thymus vulgaris)
  作者：Sandra T. Krause、Tobias G. Köllner、Julia Asbach、Jörg Degenhardt

  DOI：10.1016/j.abb.2012.12.003

  日期：2013.1

  The essential oil of Thymus vulgaris consists of a complex blend of mono- and sesquiterpenes that provides the plant with its characteristic aromatic odor. Several chemotypes have been described for thyme. In this study, we identified two enzymes of the sabinene hydrate chemotype which are responsible for the biosynthesis of its major monoterpene alcohols, (1S,2R,4S)-(Z)-sabinene hydrate and (1S,2S,4R)-(E)-sabinene hydrate. Both TPS6 and TPS7 are multiproduct enzymes that formed 16 monoterpenes and thus cover almost the whole monoterpene spectrum of the chemotype. Although the product spectra of both enzymes are similar, they form opposing enantiomers of their chiral products. Incubation of the enzymes with the potential reaction intermediates revealed that the stereospecificity of TPS6 and TPS7 is determined by the formation of the first intermediate, linalyl diphosphate. Since TPS6 and TPS7 shared an amino acid sequence identity of 85%, a mutagenesis study was employed to identify the amino acids that determine the stereoselectivity. One amino acid position had a major influence on the stereochemistry of the formed products. Based on comparative models of TPS6 and TPS7 protein structures with the GPP substrate docked in the active site pocket, the influence of this amino acid residue on the reaction mechanism is discussed. (C) 2012 Elsevier Inc. All rights reserved.
• A short and efficient synthesis of (±)-trans-sabinene hydrate
  作者：Christophe C Galopin

  DOI：10.1016/s0040-4039(01)01081-4

  日期：2001.8

  A short synthesis of sabinene hydrate is reported. It uses cheap starting materials and affordable reagents. The main product of the synthesis is trans-sabinene hydrate. (C) 2001 Elsevier Science Ltd. All rights reserved.