nootkatol | 840474-83-1

• 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: nootkatol
• 英文别名: (4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-ol
• CAS: 840474-83-1
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: GFNWRKNVTHDNPV-WMSLONTCSA-N

物化性质

• 沸点：
  316.8±42.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  nootkatol 生成 nootkatene
  参考文献：
  名称：

  Davies, Alwyn G.; Davison, Ian G. E., Journal of the Chemical Society. Perkin transactions II, 1989, p. 825 - 830

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-香柏酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.33h， 以98.3%的产率得到nootkatol
  参考文献：
  名称：

  +-香柏酮的衍生物

  摘要：

  本发明公开了一种+‑香柏酮衍生物的制备方法。本发明是以香柏枝叶中提取的+‑香柏酮为原料，经硼氢化钠还原得化合物Ⅱ，化合物Ⅱ再通过酶催化的动力学拆分反应得化合物Ⅲ以及化合物Ⅳ，或经动态动力学拆分得收率90%以上的化合物Ⅲ，化合物Ⅲ经水解可得化合物Ⅴ。本发明近一步将+‑香柏酮中的潜手性酮基变成手性羟基中心，并进一步进行拆分；本发明具备操作简单，产品收率高、光学纯度好等特点。

  公开号：

  CN106349013A

文献信息

• Selective Enzymatic Synthesis of the Grapefruit Flavor (+)-Nootkatone
  作者：Sebastian Schulz、Marco Girhard、Sarah K. Gaßmeyer、Vera D. Jäger、Daniel Schwarze、Andreas Vogel、Vlada B. Urlacher

  DOI：10.1002/cctc.201402952

  日期：2015.2

  (+)‐Nootkatone is a high‐value sesquiterpenoid known for its grapefruit‐odor impression. Its isolation from natural plant sources suffers from low yields, and chemical syntheses involve carcinogenic or hazardous compounds. Herein, a biocatalytic route for the synthesis of (+)‐nootkatone that combines two enzymes in one pot is presented. In the first step, a cytochrome P450 monooxygenase catalyzes the

  （+）-Nootkatone是一种高价值的倍半萜类，以其葡萄柚味印象而闻名。它与天然植物来源的分离产量低，化学合成涉及致癌或有害化合物。本文介绍了一种在一个锅中将两种酶结合在一起的（+）-Nootkatone的生物催化路线。第一步，细胞色素P450单加氧酶催化倍半萜（+）-瓦伦烯向中间醇Nootkatol的选择性烯丙基羟基化。第二步，通过醇脱氢酶（ADH）将Nootkatol进一步氧化为（+）-nootkatone。寻找合适的辅因子再生系统的艰巨任务是通过仔细选择适用于双功能模式的ADH的合适辅助底物而解决的。经过反应优化后， L -1和时空产率为18 mg  L -1  h -1。
• Method for separation of reaction products from catalysts
  申请人：——

  公开号：US20040014985A1

  公开（公告）日：2004-01-22

  A method separates a reaction product from an imide compound catalyst represented by Formula (1) or an altered derivative thereof in a reaction mixture obtained as a result of a reaction in the presence of the imide compound catalyst by performing an extraction process using two organic solvents separable from each other to thereby separate the reaction product into one organic solvent layer and the imide compound catalyst or an altered derivative thereof into the other organic solvent layer, respectively: 1 wherein R 1 and R 2 are each, for example, a hydrogen atom or an alkyl group, where R 1 and R 2 may be combined to form a double bond, an aromatic ring, or a non-aromatic ring; and X is an oxygen atom or a hydroxyl group. The method of the invention can efficiently and simply separate a reaction product from a catalyst and/or an altered derivative of the catalyst in a reaction mixture obtained as a result of a reaction of a substrate such as a hydrocarbon using N-hydroxyphthalimide or another imide compound as the catalyst.

  一种方法，通过使用两种可分离的有机溶剂进行萃取过程，从存在咪唑化合物催化剂的反应混合物中分离出反应产物和咪唑化合物催化剂或其改性衍生物，其中咪唑化合物催化剂由式（1）或其改性衍生物表示： 式（1）中，R1和R2分别是氢原子或烷基，R1和R2可以结合形成双键、芳香环或非芳香环；X是氧原子或羟基。 该发明的方法可以高效简单地从使用N-羟基邻苯二甲酰亚胺或其他咪唑化合物作为催化剂的底物如碳氢化合物的反应混合物中分离出反应产物和催化剂和/或催化剂的改性衍生物。
• Reaction sequence for the synthesis of nootkatone, dihydronootkatone, and tetrahydronootkatone
  申请人：Laine Roger

  公开号：US10435344B2

  公开（公告）日：2019-10-08

  An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed utilizing ozonolysis. The starting materials used in the synthesis are inexpensive and the reactions are commercially feasible and amenable to scaling up. The principal starting material, (−)-β-Pinene, is on the GRAS list (generally recognized as safe).

  本发明公开了一种利用臭氧分解法合成诺卡托酮、四氢诺卡托酮及其衍生物的廉价、立体选择性合成方法。合成过程中使用的起始原料价格低廉，反应具有商业可行性，并易于推广。主要起始原料 (-)-β-Pinene 已列入 GRAS 名单（公认安全）。
• Kabbara, Jazid; Flemming, Steffen; Nickisch, Klaus, Liebigs Annalen, 1995, # 2, p. 401 - 406
  作者：Kabbara, Jazid、Flemming, Steffen、Nickisch, Klaus、Neh, Harribert、Westermann, Juergen

  DOI：——

  日期：——
• Studies towards the synthetic applicability of biocatalytic allylic oxidations with the lyophilisate of Pleurotus sapidus
  作者：Verena Weidmann、Serge Kliewer、Marko Sick、Sergej Bycinskij、Margarethe Kleczka、Julia Rehbein、Axel G. Griesbeck、Holger Zorn、Wolfgang Maison

  DOI：10.1016/j.molcatb.2015.07.008

  日期：2015.11

  The edible fungus Pleurotus sapidus (PSA) is a particularly interesting biocatalytic system for allylic oxidation and has a remarkably broad substrate range from terpenoids to fatty acids. The oxidations are most likely catalyzed by a lipoxygenase and involve the formation of peroxides via radical intermediates in the first rate-limiting step. We provide herein a rationalization of the observed regioselectivity of these conversions by means of computational determination of bond dissociation enthalpies of a set of tailor-made spirocyclic terpenoids. It was found that only strongly activated allylic positions (BDH298 of <80 kcal/mol) with neighboring heteroatoms or with activating alkyl groups are oxidized to the corresponding unsaturated lactones or enones, respectively. With the synthesis and purification of allylic hydroperoxide intermediates, we have been able to characterize the putative direct precursors of enones in PSA oxidations. Our results suggest a two-step oxidation mechanism involving hydroperoxide intermediates which are rapidly converted to the observed enones by an enzymatic reaction. (C) 2015 Elsevier B.V. All rights reserved.