trans-5-tert-butylcyclohex-2-enol | 32591-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-5-tert-butylcyclohex-2-enol
• 英文别名: 5(e)-(tert-Butyl)-2-cyclohexenol；cis-5-tert-butylcyclohex-2-enol；5-t-butyl-2-cyclohexen-1-ol；5-tert-butylcyclohex-2-enol；5-t-butylcyclohex-2-enol；cis/trans-5-tert.butyl-2-cyclohexenol；5-Tert-butyl-2-cyclohexen-1-OL；5-tert-butylcyclohex-2-en-1-ol
• CAS: 32591-15-4
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: OOEPVZSVTNDRRX-UHFFFAOYSA-N

物化性质

• 沸点：
  218.8±19.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：

  trans-5-tert-butylcyclohex-2-enol 在 chromium(VI) oxide 、 硫酸 作用下， 生成 5-(1,1-二甲基乙基)-环己-2-烯-1-酮
  参考文献：
  名称：

  关于环状烯丙醇的二羟基化

  摘要：

  描述了一系列构象受限的烯丙基醇的制备和二羟基化（OsO 4）。通过使用二氯甲烷作为溶剂，有利于抗三醇的选择性通过氢键作用而大大降低。该原理适用于从（1S，2S）-1,2-二羟基-3-溴-3,5-环己二烯的氧化反应合成四元醇的立体选择性合成。

  DOI：

  10.1016/0040-4039(96)00558-8
• 作为产物：
  描述：

  4-(1,1-二甲基乙基)环己烯-1-基三甲基硅烷 生成 trans-5-tert-butylcyclohex-2-enol
  参考文献：
  名称：

  Regiospecific photosensitized oxygenation of vinylsilanes. A method for converting saturated ketones to 1,2-transposed allylic alcohols. Possible role of silicon in directing the regioselectivity of epoxysilane cleavage reactions

  摘要：

  DOI：

  10.1021/ja00509a084

文献信息

• Directed Dihydroxylation of Cyclic Allylic Alcohols and Trichloroacetamides Using OsO₄/TMEDA
  作者：Timothy J. Donohoe、Kevin Blades、Peter R. Moore、Michael J. Waring、Jon J. G. Winter、Madeleine Helliwell、Nicholas J. Newcombe、Geoffrey Stemp

  DOI：10.1021/jo026161y

  日期：2002.11.1

  The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.

  介绍了用OsO4 / TMEDA氧化一系列环状烯丙醇和酰胺的方法。在这些条件下，几乎在每个所研究的实施例中，氢键控制导致顺式异构体的（对映体）形成。提供了TMEDA与OsO4的双齿结合的证据，并描述了一个可能的机制。
• On the dihydroxylation of cyclic allylic alcohols
  作者：Timothy J. Donohoe、Rina Garg、Peter R. Moore

  DOI：10.1016/0040-4039(96)00558-8

  日期：1996.5

  The preparation and dihydroxylation (OsO4) of a series of conformationally constrained allylic alcohols is described. By using dichloromethane as solvent, the selectivity that favours the anti triol is substantially reduced by hydrogen-bonding effects. This principle is applied to the stereoselective synthesis of syn tetraols from the oxidation of (1S,2S)-1,2-dihydroxy-3-bromo-3,5-cyclohexadiene.

  描述了一系列构象受限的烯丙基醇的制备和二羟基化（OsO 4）。通过使用二氯甲烷作为溶剂，有利于抗三醇的选择性通过氢键作用而大大降低。该原理适用于从（1S，2S）-1,2-二羟基-3-溴-3,5-环己二烯的氧化反应合成四元醇的立体选择性合成。
• The enigmatic 1J(CH) coupling constants of allyl-type organometallic compounds
  作者：Manfred Schlosser、Ruth Lehmann、Titus Jenny

  DOI：10.1016/0022-328x(90)85407-p

  日期：1990.6

  A new attempt has been made to identify the factors responsible for the abnormally small one-bond C, H coupling constants observed for allyl, pentadienyl and heptatrienylmetal compounds. In-plane deformations (widening of the central CCC angle) should have only a small, if not negligable effect. The out-of-plane bending of hydrogen atoms appears to contribute significantly, as probably also does accumulation

  已经进行了新的尝试来鉴定引起对于烯丙基，戊二烯基和庚三烯基金属化合物异常小的单键C，H偶合常数的因素。面内变形（扩大CCC中心角）的影响应该很小，即使可以忽略不计。氢原子的平面外弯曲似乎起了重要作用，共轭结构中电子密度的积累或极化也可能如此。
• Production Of Polyketides And Other Natural Products
  申请人：Gregory Matthew Alan

  公开号：US20090253732A1

  公开（公告）日：2009-10-08

  The present invention relates to production of polyketides and other natural products and to libraries of compounds and individual novel compounds. Therefore in aspect the present invention provides 17-desmethylrapamycin and analogues thereof, methods for their production, including recombinant strains, and isolation and uses of the compounds of the invention. In a further aspect the present invention provides for the use of 17-desmethylrapamycin and analogues thereof in the induction or maintenance of immunosuppression, the stimulation of neuronal regeneration or the treatment of cancer, B-cell malignancies, fungal infections, transplantation rejection, graft vs. host disease, autoimmune disorders, diseases of inflammation vascular disease and fibrotic diseases, and in the regulation of wound healing.

  本发明涉及聚酮类化合物和其他天然产物的生产，以及化合物库和独特新化合物的制备。因此，本发明提供了17-去甲基拉帕霉素及其类似物，包括重组菌株的制备方法，以及本发明化合物的分离和用途。此外，本发明还提供了将17-去甲基拉帕霉素及其类似物用于诱导或维持免疫抑制、促进神经再生或治疗癌症、B细胞恶性肿瘤、真菌感染、移植排斥、移植物抗宿主病、自身免疫性疾病、炎症性血管疾病和纤维化疾病的调节。
• 17-Desmethylrapamycin and analogues thereof, methods for their production and their use as immunosupressants, anticancer agents, antifungal agents etc.
  申请人：Biotica Technology Limited

  公开号：EP2471797A2

  公开（公告）日：2012-07-04

  The present invention relates to production of polyketides and other natural products and to libraries of compounds and individual novel compounds. Therefore in one aspect the present invention provides 17-desmethylrapamycin and analogues thereof, methods for their production, including recombinant strains, and isolation and uses of the compounds of the invention. In a further aspect the present invention provides for the use of 17-desmethylrapamycin and analogues thereof in the induction or maintenance of immunosuppression, the stimulation of neuronal regeneration or the treatment of cancer, B-cell malignancies, fungal infections, transplantation rejection, graft vs. host disease, autoimmune disorders, diseases of inflammation vascular disease and fibrotic diseases, and in the regulation of wound healing.

  本发明涉及多酮类化合物和其他天然产物的生产，以及化合物库和单个新型化合物。因此，在一个方面，本发明提供了 17-去甲基拉帕霉素及其类似物、其生产方法（包括重组菌株）以及本发明化合物的分离和用途。在另一个方面，本发明提供了17-去甲基拉帕霉素及其类似物在诱导或维持免疫抑制、刺激神经元再生或治疗癌症、B细胞恶性肿瘤、真菌感染、移植排斥反应、移植物对宿主疾病、自身免疫性疾病、炎症性血管疾病和纤维化疾病以及调节伤口愈合中的用途。