(1R,2S,4S)-(-)-neodihydrocarveol | 53796-80-8

• 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: (1R,2S,4S)-(-)-neodihydrocarveol
• 英文别名: (1R,2S,4S)-neoisodihydrocarveol；(1S,2R,5S)-dihydrocarveol；(-)-neoisodihydrocarveol；neoisodihydrocarveol；dihydrocarveol；(1R)-1r-Methyl-4c-isopropenyl-cyclohexanol-(2c)；(1S,2R,5S)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-ol
• CAS: 53796-80-8
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: KRCZYMFUWVJCLI-UTLUCORTSA-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

安全信息

• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S)-(-)-neodihydrocarveol 在 allylic alcohol dehydrogenase from Nicotiana tabacum Tris-HCl buffer 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 Triton X-100 作用下， 以 水 为溶剂， 反应 3.0h， 生成 (1R,4S)-异二氢香芹酮
  参考文献：
  名称：

  A 38 kDa allylic alcohol dehydrogenase from the cultured cells of Nicotiana tabacum

  摘要：

  An NADP(+)-dependent alcohol dehydrogenase (allyl-ADH) was isolated from the cultured cells of Nicotiana tabacum. The allyl-ADH was found to be efficient for the dehydrogenation of secondary allylic alcohols rather than saturated secondary alcohols and it was specific for the S-stereoisomer of the alcohols. The enzyme catalyzed the reversible reaction whereby the carbonyl group of enones is reduced to the corresponding allylic alcohol or vice versa. Two possible primary structures of the allyl-ADH were deduced by the sequence analyses of full-length cDNAs (ally-ADH1 and ally-ADH2), which were cloned by the PCR method. These analyses indicated that the allyl-ADHs are composed of 343 amino acids having the molecular weights 38 083 and 37 994, respectively, and they showed approximately 70% homology to the NADP(+)-dependent oxidoreductases belonging to a plant zeta -crystallin family. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00326-5
• 作为产物：
  描述：

  (1R,4S)-异二氢香芹酮 在 glutamate dehydrogenase 、 葡萄糖 、 LfSDR₁ V₁₈₆W variant 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 aq. phosphate buffer 、 Petroleum ether 为溶剂， 反应 12.0h， 以99%的产率得到
  参考文献：
  名称：

  酮还原酶/烯还原酶催化的不对称还原立体异构合成香芹酚和二氢香芹醇

  摘要：

  手性香芹酚和二氢香芹酚是香料工业中的重要添加剂，是天然产物合成的基础。尽管在不对称催化方面取得了显着进展，但方便地获得香芹酚和二氢香芹酚的所有可能的立体异构体仍然是一个挑战。在这里，我们介绍了通过酮还原酶/烯还原酶催化的不对称还原立体合成香芹酚和二氢香芹醇。通过（R）和（S的直接不对称还原）使用酮还原酶的香芹酮，具有Prelog或anti-Prelog立体偏好，首先观察到了中度至高度非对映异构体过量（高达> 99％）的香芹酚的所有四种可能的立体异构体。然后通过烯还原酶催化的非对映选择性合成制备了二氢香芹酮的四种立体异构体。酮还原酶使获得的二氢香芹酮异构体不对称还原进一步提供了高达85％de值的所有八种立体异构体二氢香芹酚的获取途径。另外，通过使用改进的Mosher方法确定了二氢香蒲醇立体异构体的绝对构型。

  DOI：

  10.1002/cctc.201801391

文献信息

• Heterogeneous Hydroxyl-Directed Hydrogenation: Control of Diastereoselectivity through Bimetallic Surface Composition
  作者：Alexander J. Shumski、William A. Swann、Nicole J. Escorcia、Christina W. Li

  DOI：10.1021/acscatal.1c01434

  日期：2021.5.21

  surface. In this work, we demonstrate that Pd–Cu bimetallic nanoparticles with both Pd and Cu atoms distributed across the surface are capable of high conversion and diastereoselectivity in the hydroxyl-directed hydrogenation reaction of terpinen-4-ol. We postulate that the OH directing group adsorbs to the more oxophilic Cu atom while the olefin and hydrogen bind to adjacent Pd atoms, thus enabling selective

  定向氢化反应通常由均相的Rh和Ir络合物催化，其中产物的选择性取决于底物上辅助定向基团与催化剂的结合。由于缺乏对催化剂表面上底物结合取向的控制，没有一种多相催化剂能够达到相当高的方向性。在这项工作中，我们证明了Pd和Cu原子分布在整个表面上的Pd-Cu双金属纳米粒子在萜品烯-4-醇的羟基定向加氢反应中具有很高的转化率和非对映选择性。我们假设OH导向基团吸附到更具亲氧性的Cu原子上，而烯烃和氢键合到相邻的Pd原子上，
• Enantioselectivity in the Biotransformation of Mono- and Bicyclic Monoterpenoids with the Cultured Cells of<i>Nicotiana tabacum</i>
  作者：Hiroki Hamada

  DOI：10.1246/bcsj.61.869

  日期：1988.3

  The biotransformation of the enantiomeric pairs of p-menthane and bicyclo[2.2.1] and [3.1.1]heptane derivatives with the cultured cells of Nicotiana tabacum was investigated. It was found that (i) the cultured cells discriminate the enantiomers of p-menthan-2-ol and bicyclo[2.2.1]heptan-2-ol and bicyclo[3.1.1]heptan-3-ol derivatives, and enantioselectively convert these alcohols to the corresponding

  研究了对薄荷烷和双环 [2.2.1] 和 [3.1.1] 庚烷衍生物的对映体对与烟草培养细胞的生物转化。发现(i)培养的细胞区分对-薄荷醇-2-醇和双环[2.2.1]庚烷-2-醇和双环[3.1.1]庚烷-3-醇衍生物的对映异构体，并对映选择性转化将这些醇转化为相应的酮，(ii) 细胞高度还原 p-menthan-2-one 衍生物的羰基，但不还原 p-menthan-3-ones 的羰基，以及 (iii) 细胞区分双环[3.1.1]hept-2-en-4-one（verbenone）的对映异构体，并对映选择性还原（1S，5S）-对映异构体的C-C双键。
• The biotransformation of carvoxime and dihydrocarvoxime with cell suspension cultures of Nicotiana tabacum
  作者：Takayuki Suga、Toshifumi Hirata、Masayuki Futatsugi

  DOI：10.1016/s0031-9422(00)80453-7

  日期：1984.5

  Abstract In newly initiated cell suspension cultures of Nicotiana tabacum , (4 R )-(−) and (4 S )(+)-carvoximes and (1 S ,4 R )(+)-dihydrocarvoxime were hydrolysed to the corresponding ketones and then the resultant ketones were reduced to the corresponding alcohols.

  摘要 在烟草新开始的细胞悬浮培养中，(4 R )-(-) 和(4 S )(+)-香芹酮肟和(1 S ,4 R )(+)-二氢香芹酮肟被水解成相应的酮，然后生成的酮被还原为相应的醇。
• Stereoselectivity of the reduction of carvone and dihydrocarvone by suspension cells of Nicotiana tabacum
  作者：Toshifumi Hirata、Hiroki Hamada、Tadashi Aoki、Takayuki Suga

  DOI：10.1016/0031-9422(82)85179-0

  日期：——

  Abstract The biotransformation of foreign substrates with suspension cells of Nicotiana tabacum was tested with (4 R )-(−)- and (4 S )-(+)-carvones, (

  摘要 用 (4 R )-(-)- 和 (4 S )-(+)-香芹酮测试了烟草悬浮细胞对外来底物的生物转化，（
• Organic reactions in a solid matrix-VII sodium on alumina : A convenient reagent for reduction of ketones, esters and oximes
  作者：Satendra Singh、Sukh Dev

  DOI：10.1016/s0040-4020(01)80249-0

  日期：1993.1

  Sodium dispersed on alumina is described and evaluated as a convenient off-the-shelf reagent (in a wax-coated form) for reduction of ketones, esters and oximes. While isopropanol is the preferred proton donor for the reduction of ketones and oximes, t-butanol is the alcohol of choice for the reduction of esters.

  描述并分散在氧化铝上的钠是一种方便的现成试剂（蜡包衣形式），用于还原酮，酯和肟。异丙醇是用于还原酮和肟的优选质子供体，而叔丁醇是用于还原酯的选择的醇。