neo-isodihydrocarveol | 51773-45-6

• 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: neo-isodihydrocarveol
• 英文别名: (+)-Neoisodihydrocarveol；(1R,2S,5R)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-ol
• CAS: 51773-45-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: KRCZYMFUWVJCLI-IVZWLZJFSA-N

物化性质

• 保留指数：
  1220

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：

  neo-isodihydrocarveol 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 香芹烯酮(Z)-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：

  (R)-Carvone 在 glutamate dehydrogenase 、 葡萄糖 、 BmSDR₅ 、 OYE₁ W₁₁₆A, T₃₇A variant 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 aq. phosphate buffer 、 乙醇 、 Petroleum ether 为溶剂， 反应 24.0h， 生成 neo-isodihydrocarveol
  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

• Methylene-Linked Bis-NHC Half-Sandwich Ruthenium Complexes: Binding of Small Molecules and Catalysis toward Ketone Transfer Hydrogenation
  作者：José Manuel Botubol-Ares、Safa Cordón-Ouahhabi、Zakaria Moutaoukil、Isidro G. Collado、Manuel Jiménez-Tenorio、M. Carmen Puerta、Pedro Valerga

  DOI：10.1021/acs.organomet.1c00045

  日期：2021.3.22

  isolation of the nitrosyl derivative [Cp*Ru(NO)(L)][BPh4]2 (5), which was structurally characterized. The allenylidene complex [Cp*Ru═C═C═CPh2(L)][BPh4] (10) was also obtained, and it was prepared by reaction of 2 with HC≡CC(OH)Ph2 and NaBPh4 in MeOH at 60 °C. Complexes 3, 4, and 6 are efficient catalyst precursors for the transfer hydrogenation of a broad range of ketones. The dihydrogen complex 6 has

  络合物[CP * RuCl（COD）]与L H 2 Cl 2（L =双（3-甲基咪唑-2-亚基））和LiBu n在四氢呋喃中于65°C反应，制得双卡宾衍生物[CP * RuCl （L）]（2）。与此NaBPh化合物反应4下二氮在MeOH，得到不稳定的一氧化二桥连络合物[的CP *茹（大号）} 2（μ-N 2）] [BPH 4 ] 2（4）。4中的二氮配体很容易被一系列供体分子取代，形成相应的阳离子络合物[CP * Ru（X）（L）] [BPh 4 ]（X ＝ MeCN 3，H 2 6，C 2 H 4 8a，CH 2 CHCOOMe 8b，CHPh 9）。尝试从MeNO 2 / EtOH溶液中重结晶4导致亚硝酰基衍生物[CP * Ru（NO）（L）] [BPh 4 ] 2（5）的分离。所述allenylidene复杂的[CP *Ru═C═C═CPh 2（大号）] [BPH 4 ]（10）也
• Hydride-mediated homogeneous catalysis. Catalytic reduction of .alpha.,.beta.-unsaturated ketones using [(Ph3P)CuH]6 and H2
  作者：Wayne S. Mahoney、Jeffrey M. Stryker

  DOI：10.1021/ja00206a008

  日期：1989.11

  Hydride-mediated reduction of alpha},beta}-unsaturated ketones catalytic in the hydride reagent is reported using ((Phsub 3}P)CuH)sub 6} and molecular hydrogen. The reaction proceeds at room temperature and is highly regioselective, affording either the product of conjugate reduction or complete 1,4- and 1,2-reduction to the saturated alcohol, depending on reaction conditions. In the presence of

  使用((Phsub 3}P)CuH)sub 6}和分子氢报道了氢化物介导的α}，β}-不饱和酮催化还原在氢化物试剂中。该反应在室温下进行并且具有高度的区域选择性，根据反应条件提供共轭还原产物或完全 1,4-和 1,2-还原为饱和醇。在过量膦的存在下，该过程是均相和化学选择性的：即使在强制条件下，分离的双键也不会被氢化。这种新型催化还原似乎是通过高活性铜 (I) 烯醇化物和醇盐中间体对分子氢的异裂活化来进行的。
• Production of Flavours and Fragrances via Bioreduction of (4R)-(-)-Carvone and (1R)-(-)-Myrtenal by Non-Conventional Yeast Whole-Cells
  作者：Marta Goretti、Benedetta Turchetti、Maria Cramarossa、Luca Forti、Pietro Buzzini

  DOI：10.3390/molecules18055736

  日期：——

  As part of a program aiming at the selection of yeast strains which might be of interest as sources of natural flavours and fragrances, the bioreduction of (4R)-(−)-carvone and (1R)-(−)-myrtenal by whole-cells of non-conventional yeasts (NCYs) belonging to the genera Candida, Cryptococcus, Debaryomyces, Hanseniaspora, Kazachstania, Kluyveromyces, Lindnera, Nakaseomyces, Vanderwaltozyma and Wickerhamomyces was studied. Volatiles produced were sampled by means of headspace solid-phase microextraction (SPME) and the compounds were analysed and identified by gas chromatography–mass spectroscopy (GC-MS). Yields (expressed as % of biotransformation) varied in dependence of the strain. The reduction of both (4R)-(−)-carvone and (1R)-(−)-myrtenal were catalyzed by some ene-reductases (ERs) and/or carbonyl reductases (CRs), which determined the formation of (1R,4R)-dihydrocarvone and (1R)-myrtenol respectively, as main flavouring products. The potential of NCYs as novel whole-cell biocatalysts for selective biotransformation of electron-poor alkenes for producing flavours and fragrances of industrial interest is discussed.

  作为旨在筛选可能作为天然风味和香料来源的酵母菌株计划的一部分，研究了属于念珠菌属、隐球菌属、德巴利酵母属、汉逊酵母属、哈萨克斯坦酵母属、克鲁维酵母属、林德纳酵母属、中村酵母属、瓦尔德酵母属和威克汉姆酵母属的非常规酵母（NCYs）全细胞对（4R）-（-）-香芹酮和（1R）-（-）-桃金娘醛的生物还原作用。通过顶空固相微萃取（SPME）采样产生的挥发性物质，并使用气相色谱-质谱（GC-MS）进行分析和鉴定。产率（以生物转化百分比表示）因菌株而异。两种（4R）-（-）-香芹酮和（1R）-（-）-桃金娘醛的还原作用均由一些烯还原酶（ERs）和/或羰基还原酶（CRs）催化，这决定了（1R,4R）-二氢香芹酮和（1R）-桃金娘醇分别作为主要调味产品的形成。讨论了NCYs作为新型全细胞生物催化剂在选择性生物转化缺电子烯烃以生产工业感兴趣的风味和香料方面的潜力。
• 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，（
• Daucus carota and baker’s yeast mediated bio-reduction of prochiral ketones
  作者：Jhillu S. Yadav、Garudammagari S.K.K. Reddy、Gowravaram Sabitha、Avvaru D. Krishna、Attaluri R. Prasad、Hafeez-U-R-Rahaman、Katta Vishwaswar Rao、Adari Bhaskar Rao

  DOI：10.1016/j.tetasy.2007.03.009

  日期：2007.4

  has attracted much attention, from the viewpoint of green chemistry. Asymmetric reduction of indanone, tetralone and hydroxyl trimonoterpene ketones to the corresponding enantiomerically pure (S)-alcohols, using Daucus carota plant homogenate and fermented baker’s yeast cells, is described. The present study illustrates the broad substrate selectivity of the dehydrogenase enzymes present in the D. carota

  从绿色化学的观点来看，使用生物催化剂将手性酮立体选择性还原为相应的醇引起了广泛的关注。描述了使用胡萝卜（Daucus carota）植物匀浆和发酵的面包酵母细胞，将茚满酮，四氢萘酮和羟基三单萜酮不对称还原为相应的对映体纯的（S）醇。本研究说明了在合成具有广泛生物学意义的各种手性仲醇时，存在于胡萝卜中的脱氢酶的广泛的底物选择性。