(1S,2S)-cis-2-ethyl N-<2-<4-(2-hydroxy-1-cyclohexylmethyl)phenoxy>ethyl>carbamate | 158703-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,2S)-cis-2-ethyl N-<2-<4-(2-hydroxy-1-cyclohexylmethyl)phenoxy>ethyl>carbamate
• 英文别名: ethyl (1S,2S)-N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenyloxy}ethyl}carbamate；ethyl N-{2-[4-(((1S,2S)-2-hydroxycyclohexyl)methyl)phenoxy]ethyl}carbamate；ethyl N-{2-{4-[(cis-2-hydroxycyclohexyl)methyl]phenoxy}ethyl} carbamate；ethyl (1s,2s)-N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate；ethyl N-[2-[4-[[(1S,2S)-2-hydroxycyclohexyl]methyl]phenoxy]ethyl]carbamate
• CAS: 158703-36-7
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: JZHZZCDSDITRIS-RDJZCZTQSA-N

物化性质

• 沸点：
  497.7±25.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  十八烷酰氯 、 (1S,2S)-cis-2-ethyl N-<2-<4-(2-hydroxy-1-cyclohexylmethyl)phenoxy>ethyl>carbamate 在 盐酸 作用下， 以 吡啶 、 苯 为溶剂， 生成 Ethyl N-{2-{4-[(cis-2-octadecanoyloxycyclohexyl)methyl]phenoxy}ethyl} carbamate
  参考文献：
  名称：

  Esters of fatty acids and juvenoid alcohols, and a method of their preparation and use

  摘要：

  从脂肪酸和青少年醇衍生的酯的通式（I），其中X表示氧原子或NH基团，Y表示NH基团或氧原子，R表示甲基、乙基、1-丙基、2-甲基乙基或丙炔基，R'表示饱和或不饱和的烷基，其碳原子数为4至22。从脂肪酸和青少年醇衍生的酯是通过将通式（II）的青少年醇（其中X表示氧原子或NH基团，Y表示NH基团或氧原子，R表示甲基、乙基、1-丙基、2-甲基乙基或丙炔基）与通式（III）的脂肪酸氯化物进行反应而产生的：R'COCl，其中R'表示碳原子数为4至22的饱和或不饱和烷基，在连续搅拌下，在0至70°C下使用方便的溶剂（如甲苯、二甲苯或苯）和碱性催化剂（如三乙胺、吡啶或喹啉）的存在下。通式（I）的权利要求1中所要求的化合物用于控制昆虫种群密度。

  公开号：

  US20030028047A1
• 作为产物：
  描述：

  cis-2-(4-methoxymethoxybenzyl)-1-cyclohexanol 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 丁酮 、 苯 为溶剂， 反应 28.0h， 生成 (1S,2S)-cis-2-ethyl N-<2-<4-(2-hydroxy-1-cyclohexylmethyl)phenoxy>ethyl>carbamate
  参考文献：
  名称：

  衍生自2-取代的环己醇的手性类化合物

  摘要：

  手性保幼激素类似物1 - 4D是由选自由在采用微生物介导的生物转化和/或便利的底物的酶介导的转化的酶化学方法制备的，接着手性中间体的化学转化为靶向的手性化合物。研究了类黄体立体异构体1d-4d对黄粉虫（Tenebrio molitor）up的生物活性。

  DOI：

  10.1016/0957-4166(94)80119-3

文献信息

• Synthesis of chiral cycloalkanols using yeast whole cell bioreactors
  作者：Marie Zarevúcka、Zdeněk Wimmer、David Šaman、Kateřina Demnerová、Martina Macková

  DOI：10.1016/j.tetasy.2004.03.006

  日期：2004.4

  Geotrichum luduwigii, Geotrichum candidum, and Saccharomyces cerevisiae whole cells were used for bioreduction of ethyl N-12-4-[(2-oxocyclohexyl)methyl]phenoxy}ethyl} carbarn ate 1, an insect juvenile hormone bioanalog, to produce the stereoisomers of ethyl N-2-4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl} carbamate 2-5 with as high as possible enantiomeric purity ( > 99% ee for 2 and 3 in several cases). Hydrophobic polymer Amberlite XAD-7 was used for potential modification of the reaction course mediated by isoenzymes present in the yeast whole cell bioreactors. Only stereoisomers 2 and 3 of ethyl N-2-4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl} carbamate were obtained as major products of the studied enzymic process mediated by selected microorganisms. (C) 2004 Elsevier Ltd. All rights reserved.
• Enantiomeric Purity of Biodegradation Products of Juvenogens by Newly Isolated Soil Bacteria
  作者：Jaroslav Novák、Richard Tykva、Zdeněk Wimmer、Milan Pavlík、Marek Prouza、Klára Hlavsová、Marie Zarevúcka

  DOI：10.1021/jf800526a

  日期：2008.8.1

  Two bacteria were isolated from sand RQ30, characterized as Bacillus simplex and Bacillus sp. strain 05 (GenBank EU399813), and were used as biocatalysts for a hydrolytic assay of stability of the cis or trans isomers of ethyl N-2-4-[2-(butanoyl)oxycyclohexyl]methyl}phenoxy}ethyl}carbamate, which are among insect hormonogen substances (juvenogens). The stability tests were performed using simple modeling under laboratory conditions. The structures of the products were assigned as ethyl (1R,2R)-N-2-4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate and ethyl (1S,2R)-N-2-4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate on the basis of H-1 and C-13 NMR, IR, and FAB-MS analyses.
• Chiral juvenoids derived from 2-substituted cyclohexanols
  作者：Martin Rejzek、Zdenék Wimmer、Marie Zarevúcka、David Šaman、Milan Pavlík、Michaela Říčánková

  DOI：10.1016/0957-4166(94)80119-3

  日期：1994.8

  Chiral juvenoids 1 - 4d were prepared by a chemoenzymatic process consisting in employing microorganism-mediated biotransformations and/or enzyme-mediated transformation of convenient substrates, followed by a chemical transformation of the chiral intermediates into the chiral compounds targeted. Biological activity of the juvenoid stereoisomers 1d - 4d on the yellow mealworm (Tenebrio molitor) pupae

  手性保幼激素类似物1 - 4D是由选自由在采用微生物介导的生物转化和/或便利的底物的酶介导的转化的酶化学方法制备的，接着手性中间体的化学转化为靶向的手性化合物。研究了类黄体立体异构体1d-4d对黄粉虫（Tenebrio molitor）up的生物活性。
• Esters of fatty acids and juvenoid alcohols, and a method of their preparation and use
  申请人：——

  公开号：US20030028047A1

  公开（公告）日：2003-02-06

  Esters derived from fatty acids and juvenoid alcohols of the general formula (I), in which X means the oxygen atom or the NH group, Y means the NH group or the oxygen atom, R means methyl, ethyl, 1-propyl, 2-methylethyl or propargyl and R′ means saturated or unsaturated alkyl with 4 to 22 carbon atoms. Esters derived from fatty acids and juvenoid alcohols are produced by a reaction of a juvenoid alcohol of the general formula (II), in which X means the oxygen atom or the NH group, Y means the NH group or the oxygen atom and R means methyl, ethyl, 1-propyl, 2-methylethyl or propargy] with a fatty acid chloride of the general formula (Ill): R′COC1 in which R′ means saturated or unsaturated alkyl with 4 to 22 carbon atoms, under the continuous stirring, at 0 to 70° C., using a convenient solvent, as toluene, xylene or benzene and under the presence of a base catalyst, as triethylamine, pyridine or quinoline. The compounds claimed in the claim 1 of the general formula (I) are applied for the insect population density control.

  从脂肪酸和青少年醇衍生的酯的通式（I），其中X表示氧原子或NH基团，Y表示NH基团或氧原子，R表示甲基、乙基、1-丙基、2-甲基乙基或丙炔基，R'表示饱和或不饱和的烷基，其碳原子数为4至22。从脂肪酸和青少年醇衍生的酯是通过将通式（II）的青少年醇（其中X表示氧原子或NH基团，Y表示NH基团或氧原子，R表示甲基、乙基、1-丙基、2-甲基乙基或丙炔基）与通式（III）的脂肪酸氯化物进行反应而产生的：R'COCl，其中R'表示碳原子数为4至22的饱和或不饱和烷基，在连续搅拌下，在0至70°C下使用方便的溶剂（如甲苯、二甲苯或苯）和碱性催化剂（如三乙胺、吡啶或喹啉）的存在下。通式（I）的权利要求1中所要求的化合物用于控制昆虫种群密度。