(R)-2-((4-氯苯氧基)甲基)环氧乙烷 | 129098-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (R)-2-((4-氯苯氧基)甲基)环氧乙烷
• 英文名称: (R)-p-chlorophenyl glycidyl ether
• 英文别名: (R)-2-((4-chlorophenoxy)methyl)oxirane；4-chlorophenyl glycidyl ether；(2R)-2-[(4-chlorophenoxy)methyl]oxirane
• CAS: 129098-58-4
• 化学式: C₉H₉ClO₂
• 分子量: 184.622
• InChiKey: KSLSZOOZWRMSAP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-氯苯基缩水甘油醚	4-chlorophenyl 2,3-epoxypropyl ether	2212-05-7	C9H9ClO2	184.622

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-1-(tert-butylamino)-3-(4-chlorophenoxy)propan-2-ol	1394906-80-9	C13H20ClNO2	257.76

反应信息

• 作为反应物：
  描述：

  (R)-2-((4-氯苯氧基)甲基)环氧乙烷 在 三乙酰氧基硼氢化钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (R)-1-(4-chlorophenoxy)-3-(N-methyl-N-(pyrazolo[1,5-a]pyridin-3-ylmethyl)amino)propan-2-ol
  参考文献：
  名称：

  Analogs of the dopamine D4 receptor ligand FAUC 113 with planar- and central-chirality

  摘要：

  employing yeast enzymes, natural amino acids and the Jacobsen's catalyst as sources of chirality, we have synthesized pyrazolo[1,5-a]pyridine derivatives with central- and planar-chirality as analogs of the dopamine D4 receptor ligand FAUC 113. In vitro binding experiments displayed enhanced D2 and D3 affinity for both enantiomers of the [2.2]paracyclophane 3. The C-methylpiperazine (R)-4a revealed excellent D4 selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00639-0
• 作为产物：
  描述：

  4-氯苯基缩水甘油醚 在 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以61%的产率得到(R)-2-((4-氯苯氧基)甲基)环氧乙烷
  参考文献：
  名称：

  Development of β-Amino Alcohol Derivatives That Inhibit Toll-like Receptor 4 Mediated Inflammatory Response as Potential Antiseptics

  摘要：

  Toll-like receptor 4 (TLR4) induced proinflammatory signaling has been directly implicated in severe sepsis and represents an attractive therapeutic target. Herein, we report our investigations into the structure-activity relationship and preliminary drug metabolism/pharmacokinetics study of beta-amino alcohol derivatives that inhibit the TLR4 signaling pathway. Lead compounds were identified from in vitro cellular examination with micromolar potency for their inhibitory effects on TLR4 signaling and subsequently assessed for their ability to suppress the TLR4-induced inflammatory response in an ex vivo whole blood model. In addition, the toxicology, specificity, solubility, brain-blood barrier permeability, and drug metabolism of several compounds were evaluated. Although further optimizations are needed, our findings lay the groundwork for the future drug development of this class of small molecule agents for the treatment of severe sepsis.

  DOI：

  10.1021/jm2003365

文献信息

• Enantioselective α-hydroxylation of β-keto esters catalyzed by chiral S-timolol derivatives
  作者：Yuanchun Cai、Mingming Lian、Zhi Li、Qingwei Meng

  DOI：10.1016/j.tet.2012.07.003

  日期：2012.9

  derived from the β-blocker inhibitor S-timolol determined the most active catalyst of asymmetric α-hydroxylation of β-keto esters. (R)-1-(tert-butylamino)-3-(3,4,5-trimethoxyphenoxy) propan-2-ol (3k) was the most effective derivative, enantioselectively catalyzing α-hydroxylation of β-keto esters using tert-butyl hydroperoxide as the oxidant in hexane to afford the corresponding products in excellent yield

  由β-阻滞剂抑制剂S-噻吗洛尔衍生的芳氧基氨基丙醇有机催化剂的筛选确定了β-酮酯的不对称α-羟基化的最具活性的催化剂。（R）-1-（叔丁基氨基）-3-（3,4,5-三甲氧基苯氧基）丙烷-2-醇（3k）是最有效的衍生物，它使用叔-对映体催化β-酮酸酯的α-羟基化。丁基过氧化氢作为己烷中的氧化剂，以优异的收率和良好的对映选择性（高达96％的收率，88％ee）提供相应的产物。
• Novel lapachone compounds and methods of use thereof
  申请人：Ashwell Mark A.

  公开号：US20090105166A1

  公开（公告）日：2009-04-23

  The present invention provides novel tricyclic spiro-oxathiine naphthoquinone derivatives, a synthetic method for making the derivatives, and the use of the derivatives to induce cell death and/or to inhibit proliferation of cancer or precancerous cells. The naphthoquinone derivatives of the present invention are related to the compound known as β-lapachone (3,4-dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione).

  本发明提供了一种新型的三环螺-氧杂硫杂萘醌衍生物，一种制造该衍生物的方法，以及利用该衍生物诱导细胞死亡和/或抑制癌症或前癌细胞增殖的应用。本发明的萘醌衍生物与被称为β-拉帕醇（3,4-二氢-2,2-二甲基-2H-萘(1,2-b)吡喃-5,6-二酮）的化合物有关。
• An Unusual (R)-Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers
  作者：Jing Zhao、Yan-Yan Chu、Ai-Tao Li、Xin Ju、Xu-Dong Kong、Jiang Pan、Yun Tang、Jian-He Xu

  DOI：10.1002/adsc.201100031

  日期：2011.6

  ortho‐substituted phenyl glycidyl ethers and para‐nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)‐enantiopreference was unexpectedly observed for the ortho‐nitrophenyl glycidyl ether. As a proof‐of‐concept, five enantiopure epoxides (>99% ee) were obtained in high yields, and a gram‐scale preparation of

  从巨大芽孢杆菌ECU1001中克隆了一种新的环氧水解酶（BMEH），该酶具有异常的（R）-对映体选择性和很高的活性。在对位取代的苯基缩水甘油醚和对硝基苯乙烯氧化物的生物拆分中，实现了最高的对映选择性（E > 200）。值得一提的是，底物结构显着影响了酶的对映选择性，因为人们意外地观察到邻硝基硝基苯缩水甘油醚的反向（S）-对映体选择性。作为概念验证，以高收率获得了五种对映纯环氧化合物（> 99％ee），并以克级制备了（S） -邻甲基苯基缩水甘油基醚，然后成功地在几个小时内完成，这表明BMEH为光学活性的环氧化物的高效制备有吸引力的生物催化剂。
• Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide
  作者：Tadashi Ema、Maki Yokoyama、Sagiri Watanabe、Sota Sasaki、Hiromi Ota、Kazuto Takaishi

  DOI：10.1021/acs.orglett.7b01838

  日期：2017.8.4

  Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of

  在合成的手性大环化合物1中，具有3,5-双（三氟甲基）苯基乙炔基的1m是从二取代或单取代的环氧化物和CO 2对映选择性合成环状碳酸酯的最佳有机催化剂。1m的X射线晶体结构揭示了一个明确定义的手性腔，带有多个氢键位，适用于环氧化物的对映选择性活化。提议的催化循环得到DFT计算的支持。
• Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide
  作者：Chihiro Maeda、Mayato Mitsuzane、Tadashi Ema

  DOI：10.1021/acs.orglett.9b00447

  日期：2019.3.15

  triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO2. Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.

  合成了具有卤化三唑鎓单元的手性联萘联的Zn（II）卟啉作为双功能催化剂，用于动力学拆分CO 2的环氧化物。通过改变接头长度和亲核抗衡阴离子筛选了几种催化剂，优化的催化剂在环境温度下加速了对映选择性反应，从而生成了光学活性的环状碳酸酯和环氧化物。