1-cyclohexylbut-3-en-2-ol | 118040-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexylbut-3-en-2-ol
• 英文别名: 1-cyclohexyl-3-buten-2-ol
• CAS: 118040-79-2
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: XYPCFYDZWKTHRT-UHFFFAOYSA-N

物化性质

• 沸点：
  216.5±8.0 °C(Predicted)
• 密度：
  0.907±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  3
• 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：

  1-cyclohexylbut-3-en-2-ol 在 二溴亚砜 、 正丁基锂 、 1,5-已二烯 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 0.25h， 生成 (E,2S)-6-cyclohexyl-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methyl-2-propan-2-ylhex-4-enamide
  参考文献：
  名称：

  Formal, Stereoselective Synthesis of Hydroxyethylene Dipeptide Isosteres Utilizing Pseudoephedrine Amides

  摘要：

  DOI：

  10.1021/jo9707951
• 作为产物：
  描述：

  2-环己基乙醇 在 phosphorus pentoxide 、 二甲基亚砜 、 1-叠氮基乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-cyclohexylbut-3-en-2-ol
  参考文献：
  名称：

  使用手性酰基恶唑烷酮的立体选择性溴内酯化有效合成对应于羟乙烯二肽等排物的γ-内酯

  摘要：

  一种有效的合成路线描述于γ内酯对应于二肽电子等排体（2 ，4 ，5 ）-5-氨基-6-环己基-4-羟基-2-异丙基己酸，其中立体化学控制是通过参与实现立体选择性溴内酯化反应中的手性酰基恶唑烷酮。

  DOI：

  10.1016/s0040-4039(01)80674-2

文献信息

• Allylation of Nitrosobenzene with Pinacol Allylboronates. A Regioselective Complement to Peroxide Oxidation
  作者：Robert E. Kyne、Michael C. Ryan、Laura T. Kliman、James P. Morken

  DOI：10.1021/ol101472k

  日期：2010.9.3

  Addition of nitrosobenzene to pinacol allylboronates leads to oxidation of the organoboron with concomitant rearrangement of the substrate alkene. This reaction appears to proceed by allylboration of the nitroso group in analogy to carbonyl and imine allylation reactions. Remarkably, the N−O bond is cleaved during the reaction such that simple alcohols are the final reaction product.

  将亚硝基苯加入频哪醇烯丙基硼酸酯导致有机硼氧化，同时伴随底物烯烃的重排。该反应似乎通过亚硝基的烯丙基硼化进行，类似于羰基和亚胺烯丙基化反应。值得注意的是，NO 键在反应过程中被裂解，最终反应产物是简单的醇。
• Processes for the preparation of 5-amino-4-hydroxyvaleric acid
  申请人：Ciba-Geigy Corporation

  公开号：US04898977A1

  公开（公告）日：1990-02-06

  The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.

  该发明涉及一种用于制备5-氨基-4-羟基戊酸衍生物的新工艺和中间体，其化学式为：其中R.sup.1代表氢、可选择地取代的烷基、环烷基、环烷基-较低烷基、芳基、芳基-较低烷基或天然氨基酸的基团，R.sup.2代表氢、可选择地取代的烷基、环烷基、环烷基-较低烷基、芳基、芳基-较低烷基、氨基、羟基、巯基、亚砜基、磺酰基或天然氨基酸的基团，R.sup.3代表可选择地取代的羟基或氨基，通过适当烯丙基酯的重排、所得γ、δ-不饱和酸的卤内酯化或其适当衍生物的卤素与含氮亲核试剂的交换、环内酯开环和氨基的释放。化合物I的起始物质用于制备具有抗高血压作用的肾素抑制剂。
• Process for the preparation of haloalkyllactones
  申请人：Imperial Chemical Industries PLC

  公开号：US05254697A1

  公开（公告）日：1993-10-19

  The invention provides a novel process for the manufacture of enantiomerically-pure halolactones of the formula I which are useful for the production of certain 5-amino-4-hydroxyvaleric acid derivatives, themselves valuable intermediates in the production of compounds which are renin inhibitors. The process involves a diastereoselective alkylation of an oxazolidinone of the formula III, followed by a highly stereoselective and novel halolactonisation of an oxazolidinone of the formula II. Certain of the oxazolidinones of the formula II are novel and are provided as a further feature of the invention. The invention also provides a novel process for the production of the pharmaceutically-useful 5-amino-4-hydroxyvaleric acid derivatives of formula VI.

  本发明提供了一种制备对映纯卤代内酯（式I）的新工艺，该工艺对于生产某些5-氨基-4-羟基戊酸衍生物非常有用，这些衍生物本身是制备肾素抑制剂化合物的有价值中间体。该工艺涉及到式III的峰异构体烷基化，然后是式II的高度立体选择性和新颖的卤代内酯化反应。其中，某些式II的峰异构体是新颖的，并作为本发明的另一个特征提供。本发明还提供了一种制备具有药用价值的式VI的5-氨基-4-羟基戊酸衍生物的新工艺。
• Processes for the preparation of 5-amino-4-hydroxy-valeric acid
  申请人：Ciba-Geigy Corporation

  公开号：US05010189A1

  公开（公告）日：1991-04-23

  The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonization of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.

  本发明涉及一种制备5-氨基-4-羟基戊酸衍生物的新型方法和中间体，其化学式为##STR1##其中R.sup.1表示氢，可选择性地取代烷基，环烷基，环烷基-低烷基，芳基，芳基-低烷基或天然氨基酸的基团，R.sup.2表示氢，可选择性地取代烷基，环烷基，环烷基-低烷基，芳基，芳基-低烷基，氨基，羟基，硫醇基，亚磺酰基或天然氨基酸的基团，R.sup.3表示可选择性地取代的羟基或氨基，通过适当的烯丙酸酯的sigma-转位，γ，δ-不饱和酸或其适当衍生物的卤代内酯化，卤素与含氮亲核试剂的交换，开环内酯环并释放氨基的方法制备。化合物I的式是制备抑制肾素的起始材料，具有降压作用。
• Iridium-catalyzed enantioselective alkynylation and kinetic resolution of alkyl allylic alcohols
  作者：Jia Guo、Hao-Ran Ma、Wen-Bin Xiong、Luoyi Fan、You-Yun Zhou、Henry N. C. Wong、Jian-Fang Cui

  DOI：10.1039/d2sc04892b

  日期：——

  components towards the synthesis of prostaglandins and naturally occurring matsutakeols, which are difficult to access via other asymmetric reactions. Mechanistic studies revealed that the efficient kinetic resolution might be due to the significant distinction of the η2-coordination between the (R)- and (S)-allylic alcohols with the iridium/(phosphoramidite, olefin) complex.

  在此，我们报告了烷基烯丙醇的有效动力学拆分，这是通过烷基烯丙醇与炔基三氟硼酸钾的铱催化对映选择性炔基化实现的。获得了具有各种官能团的各种手性 1,4-烯炔和未反应的富含对映体的烯丙醇，具有出色的对映选择性和高动力学分辨率性能（s因子高达 922）。此外，该方法对于制备一些有用的光学纯烷基烯丙醇特别有效，例如合成前列腺素和天然存在的松茸酚的关键成分，这些成分很难通过其他不对称反应。机理研究表明，有效的动力学拆分可能是由于 ( R )- 和 ( S )- 烯丙醇与铱/（亚磷酰胺，烯烃）络合物之间的η 2配位的显着差异。