trans-2-hydroxy-2,3-dihydrocitral | 55035-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2-hydroxy-2,3-dihydrocitral
• 英文别名: 7-hydroxy-3,7-dimethyl-2-octenal；2.6-dimethyl-octen-(6)-ol-(2)-al-(8)；Citralhydrat；7-hydroxy-3,7-dimethyl-oct-2-en-1-al；3,7-Dimethyl-7-Hydroxy-octen-(2)-al-(1)；7-Hydroxycitral；(E)-7-hydroxy-3,7-dimethyloct-2-enal
• CAS: 55035-66-0
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: HFFCMXBSDHGUPP-RMKNXTFCSA-N

物化性质

• 沸点：
  110-113 °C(Press: 1 Torr)
• 密度：
  0.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2-hydroxy-2,3-dihydrocitral 在 kieselguhr 、 镍 氢气 、 potassium iodide 作用下， 以 异丙醇 为溶剂， 生成 羟基香茅醛
  参考文献：
  名称：

  Erman, M. B.; Golovacheva, E. V.; Gulyi, S. E., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 2.1, p. 219 - 221

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 sodium hydroxide 、 硫酸 、 sodium sulfite 作用下， 以 水 为溶剂， 生成 trans-2-hydroxy-2,3-dihydrocitral
  参考文献：
  名称：

  Erman, M. B.; Golovacheva, E. V.; Gulyi, S. E., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 2.1, p. 219 - 221

  摘要：

  DOI：

文献信息

• CATALYST FOR ASYMMETRIC HYDROGENATION AND METHOD FOR MANUFACTURING OPTICALLY ACTIVE CARBONYL COMPOUND USING THE SAME
  申请人：YAMADA Shinya

  公开号：US20120136176A1

  公开（公告）日：2012-05-31

  The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

  本发明提供了一种用于通过选择性不对称加氢α，β-不饱和羰基化合物制备光学活性羰基化合物的催化剂，该催化剂在反应混合物中不溶解，并提供了制备相应光学活性羰基化合物的方法。特别地，该发明提供了一种催化剂，通过选择性不对称加氢柠檬醛、香叶醛或柠檬醛制备出用作香料或芳香剂的光学活性香茅醛。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，包括：来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种金属负载物质，其中至少一种金属负载在一种载体上；一种光学活性肽化合物；和一种酸，还涉及使用该催化剂制备光学活性羰基化合物的方法。
• CATALYST FOR ASYMMETRIC HYDROGENATION
  申请人：MAEDA Hironori

  公开号：US20100324338A1

  公开（公告）日：2010-12-23

  This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table is supported on a support, an optically active cyclic nitrogen-containing compound and an acid.

  这项发明旨在通过对α，β-不饱和羰基化合物进行选择性不对称加氢，特别是通过对柠檬醛、香叶醛或柠檬醛进行选择性不对称加氢，从而提供用作香料或香精的有用的光学活性香茅醛的催化剂，该香茅醛是一种光学活性羰基化合物；以及生产相应的光学活性羰基化合物的方法。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，其包括来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种来自周期表第8至第10族金属的金属负载物质，该金属负载在一种支撑物上，还包括光学活性的含氮环化合物和酸。
• A SIMPLE CONVERSION OF<i>N</i>,<i>N</i>-DIMETHYL-2-ALKENYLAMINE TO 2-ALKENAL
  作者：Kunihiko Takabe、Takashi Yamada、Takao Katagiri

  DOI：10.1246/cl.1982.1987

  日期：1982.12.5

  Treatment of N,N-dimethyl-2-alkenylamine with 30% H2O2 followed by acetic anhydride affords 2-alkenal (α,β-unsaturated aldehyde) in good isolated yield.

  对N,N-二甲基-2-烯基胺进行30%的过氧化氢处理后，再用乙酸酐反应，可以获得良好分离产率的2-烯醛（α,β-不饱和醛）。
• ASYMMETRIC HYDROGENATION CATALYST
  申请人：Takasago International Corporation

  公开号：EP2353714A1

  公开（公告）日：2011-08-10

  Provided is a catalyst for producing an optically active aldehyde by selective asymmetric hydrogenation of an α, β-unsaturated aldehyde, particularly a catalyst that is insoluble in the reaction mixture and is used to obtain optically active citronellal, which is useful as a fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. Also provided is a method for producing the corresponding optically active aldehyde. The α, β-unsaturated aldehyde is subjected to asymmetric hydrogenation using a solid catalyst comprising an optically active compound and a metal-supporting product wherein a carrier supports at least one metal selected from the group consisting of the elements in Groups 8 through 10 of the Periodic Table.

  本发明提供了一种通过选择性不对称氢化α，β-不饱和醛来生产光学活性醛的催化剂，特别是一种不溶于反应混合物的催化剂，可用于通过选择性不对称氢化柠檬醛、香叶醇或橙花醛来获得光学活性香茅醛，这种香茅醛可用作香料。此外，还提供了一种生产相应光学活性醛的方法。α，β-不饱和醛使用固体催化剂进行不对称氢化，固体催化剂由光学活性化合物和金属支持产物组成，其中载体支持至少一种选自元素周期表第 8 至 10 族元素组成的组的金属。
• HOMOGENEOUS ASYMMETRIC HYDROGENATION CATALYST
  申请人：Takasago International Corporation

  公开号：EP2543437A2

  公开（公告）日：2013-01-09

  The present invention provides a catalyst for producing optically active aldehyde or optically active ketone, as an optically active carbonyl compound, by selectively asymmetrically hydrogenating an α, β-unsaturated carbonyl compound, and in particular, a catalyst insoluble in a reaction mixture for obtaining optically active citronellal useful as a flavoring by selectively asymmetrically hydrogenating citral, geranial or neral, and a method for producing the corresponding optically active carbonyl compound. In particular, the present invention provides a method for producing citronellol of identical optical isomers regardless of a mixing ratio of neral and geranial in the asymmetric hydrogenation of citral. In the present invention, the α, β-unsaturated carbonyl compound is asymmetrically hydrogenated using a catalyst including a complex of at least one transition metal selected from transition metals belonging to Group 8 to Group 10 of the Periodic Table, and an optically active cyclic nitrogen-containing compound, and an acid if necessary.

  本发明提供了一种通过选择性不对称氢化α，β-不饱和羰基化合物来生产光学活性醛或光学活性酮，作为光学活性羰基化合物的催化剂，特别是提供了一种不溶于反应混合物的催化剂，用于通过选择性不对称氢化柠檬醛、香叶醇或香叶酯来获得用作香料的光学活性香茅醛，以及生产相应光学活性羰基化合物的方法。特别是，本发明提供了一种在柠檬醛的不对称氢化过程中，无论香叶醇和香叶酯的混合比例如何，都能生产出相同光学异构体的香茅醇的方法。在本发明中，α，β-不饱和羰基化合物使用一种催化剂进行不对称氢化，该催化剂包括至少一种选自属于元素周期表第 8 族至第 10 族的过渡金属的络合物和一种光学活性环状含氮化合物，必要时还包括一种酸。