(1S,2R,4R)-(-)-2-tert-butoxy-1-isopropyl-4-methylcyclohexane | 34350-47-5

• 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: (1S,2R,4R)-(-)-2-tert-butoxy-1-isopropyl-4-methylcyclohexane
• 英文别名: (1S,2R,4R)-2-t-butoxy-1-isopropyl-4-methylcyclohexane；(1S,2R,4R)-4-methyl-2-[(2-methylpropan-2-yl)oxy]-1-propan-2-ylcyclohexane
• CAS: 34350-47-5
• 化学式: C₁₄H₂₈O
• 分子量: 212.376
• InChiKey: GVVHHMCCQBLGPZ-FRRDWIJNSA-N

物化性质

• 沸点：
  234.2±8.0 °C(Predicted)
• 密度：
  0.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R)-(-)-2-tert-butoxy-1-isopropyl-4-methylcyclohexane 在 cerium(III) chloride sodium iodide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以100%的产率得到L-薄荷醇
  参考文献：
  名称：

  叔丁基醚：酒精保护小组的复兴。用氯化铈（III）/碘化钠轻松裂解

  摘要：

  的叔丁氧基衍生物是最未充分利用的醇保护基团中的一个。在开发出简单易用的引入方案后，我们在这里提供了一种简单的程序，可通过在CH 3 CN中用无水CeCl 3和NaI处理将其除去。该方法导致脂族和芳族叔丁基醚的成功裂解，并且与分子中存在的各种其他官能团和保护基团相容。

  DOI：

  10.1002/adsc.200505469
• 作为产物：
  描述：

  L-薄荷醇 、 二碳酸二叔丁酯 在 magnesium(II) perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 以70%的产率得到(1S,2R,4R)-(-)-2-tert-butoxy-1-isopropyl-4-methylcyclohexane
  参考文献：
  名称：

  在高氯酸镁存在下，碳酸二叔丁酯（Boc2O）与醇的异常和意外反应。叔丁基醚的新的通用路线。

  摘要：

  [反应：见正文]据报道，一种新的温和的保护叔丁醚醇的方法。反应与Mg（ClO4）2和Boc2O进行，显示出一般的适用性。也已经重新考虑了叔丁基醚的脱保护。初步结果表明，CeCl3 x 7H2O / NaI体系是非常适合去除它们的催化剂。

  DOI：

  10.1021/ol047704o

文献信息

• Saccharin sulfonic acid catalyzed N-Boc protection of amines and formation of tert-butyl ethers from alcohols
  作者：F. Shirini、M. A. Zolfigol、M. Abedini

  DOI：10.1007/bf03246047

  日期：2010.9

  (SaSA), as a stable reagent is easily prepared by the reaction of saccharin with neat chlorosulfonic acid at room temperature. This compound is able to catalyze conversion of amines to their corresponding N-Boc protected amines with (Boc)2O. Alcohols were also converted to their corresponding tert-butyl ethers. All reactions took place under mild conditions giving the desired products in good to high

  通过在室温下使糖精与纯净的氯磺酸反应，可以容易地制备作为稳定试剂的糖精磺酸（SaSA）。该化合物能够用（Boc）2 O催化胺转化为其相应的N- Boc保护的胺。醇也被转化为其相应的叔丁基醚。所有反应均在温和条件下进行，以高至高收率得到所需产物。
• Gold(I)-Catalyzed Synthesis of Unsymmetrical Ethers Using Alcohols as Alkylating Reagents
  作者：Yongxiang Liu、Xiaoyu Wang、Yanshi Wang、Chuan Du、Hui Shi、Shengfei Jin、Chongguo Jiang、Jianyong Xiao、Maosheng Cheng

  DOI：10.1002/adsc.201401097

  日期：2015.3.23

  microwave‐irradiated alcohol‐protecting strategy based on gold catalysis utilizing benzyl alcohol, tert‐butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen‐18 isotope labelled alcohols assisted by

  基于苄基醇，叔丁醇和三苯甲醇作为烷基化试剂的金催化的微波辐射醇保护策略已经被开发出来。对于大多数选定的醇，该保护策略具有宽泛的官能团耐受性和令人满意的产率。在GC-MS技术和化学动力学实验的辅助下，用氧18同位素标记的醇探索了这种转变的机理。该策略为有机合成中的苄基，叔丁基和三苯甲基醚的制备提供了一种有效，直接和替代的方法。
• A New, Practical and Efficient Method for Protecting Alcohols as tert-Butyl Ethers
  作者：Ernesto Occhiato、Cristina Prandi、Alessandro Barge、Dina Scarpi、Silvia Tabasso、Paolo Venturello

  DOI：10.1055/s-0029-1219360

  日期：2010.3

  A new method for protecting alcohols as tert-butyl ethers is reported. The reaction is performed in tert-butyl acetate in the presence of a catalytic amount of HClO 4 . The process is extremely efficient and primary and secondary alcohols as well as diols are protected under very mild conditions. Remarkably, tert-butyl acetate can be easily recovered after the workup of the reaction and recycled.

  报道了一种将醇类保护为叔丁基醚的新方法。该反应在催化量的HClO 4 存在下在乙酸叔丁酯中进行。该过程非常有效，伯醇和仲醇以及二醇在非常温和的条件下得到保护。值得注意的是，乙酸叔丁酯在反应后很容易回收并循环使用。
• Prodrug of amino acid derivative
  申请人：TAISHO PHARMACEUTICAL CO., LTD

  公开号：US10464884B2

  公开（公告）日：2019-11-05

  Provided is an amino acid derivative prodrug represented by general formula (I-A) that is a prodrug form of an amino acid derivative which is a group 2 metabotropic glutamate receptor antagonist, or a pharmaceutically acceptable salt thereof. More specifically, provided is an amino acid derivative prodrug represented by general formula (I-A) that is a preventive or therapeutic drug for mood disorders (including depression and bipolar disorder), anxiety disorder, cognitive disorders, developmental disorders, Alzheimer's disease, Parkinson's disease, movement disorders associated with muscular rigidity, sleep disorders, Huntington's chorea, eating disorders, drug dependence, epilepsy, brain infarction, cerebral ischemia, cerebral insufficiency, cerebral edema, spinal cord disorders, head trauma, inflammation and immune-related diseases, and so on.

  本发明提供了一种由通式（I-A）表示的氨基酸衍生物原药，它是第 2 组代谢谷氨酸受体拮抗剂的氨基酸衍生物的原药形式，或其药学上可接受的盐。 更具体地说，所提供的通式（I-A）所代表的氨基酸衍生物原药是一种预防或治疗药物，可用于治疗情绪障碍（包括抑郁症和双相情感障碍）、焦虑症、认知障碍、发育障碍、阿尔茨海默病、帕金森病、与肌肉僵硬相关的运动障碍、与肌肉僵硬有关的运动障碍、睡眠障碍、亨廷顿舞蹈症、饮食失调、药物依赖、癫痫、脑梗塞、脑缺血、脑供血不足、脑水肿、脊髓疾病、头部创伤、炎症和免疫相关疾病等。
• Prodrug amino acid derivative
  申请人：TAISHO PHARMACEUTICALS CO., LTD.

  公开号：US10689327B2

  公开（公告）日：2020-06-23

  Provided is an amino acid derivative prodrug represented by general formula (I-A) that is a prodrug form of an amino acid derivative which is a group 2 metabotropic glutamate receptor antagonist, or a pharmaceutically acceptable salt thereof. More specifically, provided is an amino acid derivative prodrug represented by general formula (I-A) that is a preventive or therapeutic drug for mood disorders (including depression and bipolar disorder), anxiety disorder, cognitive disorders, developmental disorders, Alzheimer's disease, Parkinson's disease, movement disorders associated with muscular rigidity, sleep disorders, Huntington's chorea, eating disorders, drug dependence, epilepsy, brain infarction, cerebral ischemia, cerebral insufficiency, cerebral edema, spinal cord disorders, head trauma, inflammation and immune-related diseases, and so on.

  本发明提供了一种由通式（I-A）表示的氨基酸衍生物原药，它是第 2 组代谢谷氨酸受体拮抗剂的氨基酸衍生物的原药形式，或其药学上可接受的盐。 更具体地说，所提供的通式（I-A）所代表的氨基酸衍生物原药是一种预防或治疗药物，可用于治疗情绪障碍（包括抑郁症和双相情感障碍）、焦虑症、认知障碍、发育障碍、阿尔茨海默病、帕金森病、与肌肉僵硬相关的运动障碍、与肌肉僵硬有关的运动障碍、睡眠障碍、亨廷顿舞蹈症、饮食失调、药物依赖、癫痫、脑梗塞、脑缺血、脑供血不足、脑水肿、脊髓疾病、头部创伤、炎症和免疫相关疾病等。