(-)-isopulegol

• 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: (-)-isopulegol
• 英文别名: (-)-isapulegol；(1R,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: ZYTMANIQRDEHIO-RCAUJQPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (-)-isopulegol 在 50percent NiO, 17percent CuO, 30.5percent ZrO₂, 1.5percent MoO₃, 1percent graphite; activated by H₂ at 180 C 氢气 作用下， 80.0 ℃ 、4.0 MPa 条件下， 生成 D-薄荷醇 、 L-薄荷醇
  参考文献：
  名称：

  METHOD FOR PRODUCING OPTICALLY ACTIVE, RACEMIC MENTHOL

  摘要：

  该发明涉及一种特别经济的生产薄荷醇的整体方法，具体用于生产光学活性、基本上对映异构和顺反异构纯的L-薄荷醇和混合薄荷醇，从廉价的工业规模起始原料柠檬醛开始。该方法包括以下步骤：a.1）将柠檬醛和/或莰醛催化氢化得到柠檬醛醇，b.1）在酸性催化剂存在下将柠檬醛醇环化为异薄荷醇，c.1）通过结晶纯化异薄荷醇，d.1）将异薄荷醇催化氢化得到薄荷醇。

  公开号：

  US20100249467A1

文献信息

• METHOD FOR SYNTHESIZING OPTICALLY ACTIVE CARBONYL COMPOUNDS
  申请人：BASF SE

  公开号：US20180057437A1

  公开（公告）日：2018-03-01

  The present invention relates to a process for the preparation of an optically active carbonyl compound by asymmetric hydrogenation of a prochiral α,β-unsaturated carbonyl compound with hydrogen in the presence of at least one optically active transition metal catalyst that is soluble in the reaction mixture and which has rhodium as catalytically active transition metal and a chiral, bidentate bisphosphine ligand, wherein the reaction mixture during the hydrogenation of the prochiral α,β-unsaturated carbonyl compound additionally comprises at least one compound of the general formula (I): in which R 1 , R 2 : are identical or different and are C 6 - to C 10 -aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C 1 - to C 6 -alkyl, C 3 - to C 6 -cycloalkyl, C 6 - to C 10 -aryl, C 1 - to C 6 -alkoxy and amino; Z is a group CHR 3 R 4 or aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C 1 - to C 6 -alkyl, C 3 - to C 6 -cycloalkyl, C 6 - to C 10 -aryl, C 1 - to C 6 -alkoxy and amino, wherein R 3 and R 4 are as defined in the claims and the description.

  本发明涉及一种通过在至少一种可溶于反应混合物中的光学活性过渡金属催化剂的存在下，将可溶性光学活性过渡金属铑和手性双膦配体作为催化活性过渡金属的α，β-不对称氢化的可半手性α，β-不饱和羰基化合物与氢气反应制备光学活性羰基化合物的方法。在氢化可半手性α，β-不饱和羰基化合物的过程中，反应混合物中还包括至少一种符合一般式（I）的化合物：其中 R1、R2：相同或不同，为未取代或带有一个或多个（例如1、2、3、4或5个）C6到C10芳基取代基的化合物，所述取代基选自C1到C6烷基、C3到C6环烷基、C6到C10芳基、C1到C6烷氧基和氨基；Z是一种基团CHR3R4或未取代或带有一个或多个（例如1、2、3、4或5个）取代基的芳基，所述取代基选自C1到C6烷基、C3到C6环烷基、C6到C10芳基、C1到C6烷氧基和氨基，其中R3和R4如权利要求和说明书中定义。
• Method for the Production of Optically Active Carbonyl
  申请人：Jakel Christoph

  公开号：US20080269528A1

  公开（公告）日：2008-10-30

  The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating α,β-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand. The present invention especially relates to a process for preparing optically active aldehydes or ketones, in particular citronellal, by asymmetrically hydrogenating the corresponding optically active α,β-unsaturated aldehydes or ketones.

  本发明涉及一种通过在存在可溶于反应混合物中并具有至少一个一氧化碳配体的光学活性过渡金属催化剂的情况下，对α，β-不饱和羰基化合物进行不对称氢化的方法。本发明特别涉及一种通过对相应的光学活性α，β-不饱和醛或酮进行不对称氢化而制备光学活性醛或酮的方法，特别是柠檬醛。
• PROCESS FOR PREPARATION OF MENTHOL BY HYDROGENATION OF ISOPULEGOL
  申请人：Gralla Gabriele

  公开号：US20100191021A1

  公开（公告）日：2010-07-29

  The present invention relates to a process for preparing racemic or optically active menthol by catalytically hydrogenating racemic or optically active isopulegol in the presence of hydrogen and catalysts which comprise nickel-, copper-, zirconium- and molybdenum-containing compounds. The present invention relates specifically to a corresponding process far continuously catalytically hydrogenating L-isopulegol to L-menthol.

  本发明涉及一种通过在氢气和催化剂存在下催化氢化外消旋或光学活性异薄荷醇制备外消旋或光学活性薄荷脑的方法，所述催化剂包括镍、铜、锆和钼化合物。本发明特别涉及一种相应的方法，用于连续催化氢化L-异薄荷醇制备L-薄荷脑。
• Method for the Production of Enriched Isopulegol
  申请人：Rauls Matthias

  公开号：US20080214877A1

  公开（公告）日：2008-09-04

  The present invention relates to a process for preparing enriched isopulegol by crystallization from a melt comprising isopulegol. The invention relates specifically to a process for preparing enantiomerically enriched n-isopulegol proceeding from optically active isopulegol having a relatively low enantiomeric excess by crystallization from the melt. The invention further relates to a process for preparing menthol proceeding from enantiomerically and/or diastereomerically enriched n-isopulegol prepared by crystallization from the melt.

  本发明涉及一种从含有异莪醇的熔体中通过结晶制备富集的异莪醇的方法。具体地，本发明涉及一种从具有相对较低对映体过量的光学活性异莪醇通过熔体结晶制备对映富集的n-异莪醇的方法。本发明还涉及一种从通过熔体结晶制备的对映富集的n-异莪醇制备薄荷醇的方法。
• Method For The Production Of Menthol
  申请人：Bergner Eike Johannes

  公开号：US20080139852A1

  公开（公告）日：2008-06-12

  Processes comprising: (a) enantioselectively hydrogenating a starting material comprising a component selected from geraniol, nerol and mixtures thereof to form optically active citronellol; (b) converting the optically active citronellol to optically active citronellal; (c) cyclizing the optically active citronellal to form a mixture comprising optically active isopulegol; and (d) subjecting the mixture to further processing comprising: (i) separating the optically active isopulegol from the mixture and hydrogenating the separated optically active isopulegol to form optically active menthol; or (ii) hydrogenating the optically active isopulegol in the mixture to form optically active menthol and separating the optically active menthol from the mixture.

  过程包括：(a)对包含香叶醇、柠檬叶醇或它们的混合物中的组分进行对映选择性氢化，以形成光学活性的香茅醇；(b)将光学活性的香茅醇转化为光学活性的香茅醛；(c)环化光学活性的香茅醛，形成包含光学活性异莪麝醇的混合物；(d)对混合物进行进一步处理，包括：(i)从混合物中分离出光学活性的异莪麝醇，并对分离出的光学活性异莪麝醇进行氢化，以形成光学活性的薄荷醇；或者(ii)对混合物中的光学活性异莪麝醇进行氢化，以形成光学活性的薄荷醇，并从混合物中分离出光学活性的薄荷醇。