(3-benzyloxiran-2-yl)methanol | 85531-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-benzyloxiran-2-yl)methanol
• 英文别名: 4-phenyl-2,3-epoxy-1-butanol；(3-Benzyloxiran-2-yl) methanol
• CAS: 85531-71-1
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: XJBQHGGFOBLJDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-benzyloxiran-2-yl)methanol 在 红铝 作用下， 以 四氢呋喃 为溶剂， 生成 (±)-4-phenylbutane-1,3-diol
  参考文献：
  名称：

  2,3-环氧醇的区域选择性还原

  摘要：

  用双（2-甲氧基乙氧基）氢化铝钠（Red-al）将3-取代的2，3-环氧醇区域选择性还原成1，3-二醇是这些替代物的一般反应。

  DOI：

  10.1016/s0040-4039(00)85648-8
• 作为产物：
  描述：

  (2E)-4-phenylbut-2-en-1-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以88%的产率得到(3-benzyloxiran-2-yl)methanol
  参考文献：
  名称：

  [EN] A PROCESS FOR SYNTHESIS OF SYN AZIDO EPOXIDE AND ITS USE AS INTERMEDIATE FOR THE SYNTHESIS OF AMPRENAVIR & SAQUINAVIR
  [FR] PROCÉDÉ POUR LA SYNTHÈSE D' AZIDO-ÉPOXYDE SYNTHÉTIQUE ET SON UTILISATION EN TANT QU'INTERMÉDIAIRE DE LA SYNTHÈSE D'AMPRÉNAVIR ET DE SAQUINAVIR

  摘要：

  公开号：

  WO2013105118A8

文献信息

• PROCESS FOR SYNTHESIS OF SYN AZIDO EPOXIDE AND ITS USE AS INTERMEDIATE FOR THE SYNTHESIS OF AMPRENAVIR & SAQUINAVIR
  申请人：Council of Scientific & Industrial Research

  公开号：US20150011782A1

  公开（公告）日：2015-01-08

  Disclosed herein is a novel route of synthesis of syn azide epoxide of formula 5, which is used as a common intermediate for asymmetric synthesis of HIV protease inhibitors such as Amprenavir, Fosamprenavir, Saquinavir and formal synthesis of Darunavir and Palinavir obtained by Cobalt-catalyzed hydrolytic kinetic resolution of racemic anti-(2SR,3SR)-3-azido-4-phenyl-1,2-epoxybutane (azido-epoxide).

  本文披露了一种合成公式5的syn叠氮环氧化物的新路线，该化合物被用作HIV蛋白酶抑制剂的不对称合成的常见中间体，如Amprenavir、Fosamprenavir、Saquinavir以及通过钴催化的拆分手性反式-(2SR,3SR)-3-叠氮-4-苯基-1,2-环氧丁烷(叠氮环氧化物)合成Darunavir和Palinavir。
• FITNESS ASSAY AND ASSOCIATED METHODS
  申请人：ERICKSON W. John

  公开号：US20080085918A1

  公开（公告）日：2008-04-10

  The present invention provides an assay for determining the biochemical fitness of a biochemical species in a mutant replicating biological entity relative to its predecessor. The present invention further provides a continuous fluorogenic assay for measuring the anti-HIV protease activity of protease inhibitor. The present invention also provides a method of administering a therapeutic compound that reduces the chances of the emergence of drug resistance in therapy. The present invention also provides a compound of formula (I) or a pharmaceutically acceptable salt, a prodrug, a composition, or an ester thereof, wherein A is a group of formulas (A), (B), (C) or (D); R 1 , R 2 , R 3 , R 5 or R 6 is H, or an optionally substituted and/or heteroatom-bearing alkyl, alkenyl, alkynyl, or cyclic group; Y and/or Z are CH 2 , O, S, SO, SO 2 , amino, amides, carbamates, ureas, or thiocarbonyl derivatives thereof, optionally substituted with an alkyl, alkenyl, or alkynyl group; n is from 1 to 5; X is a bond, an optionally substituted methylene or ethylene, an amino, O or S; Q is C(O), C(S), or SO 2 ; m is from 0 to 6; R 4 is OH, ═O (keto), NH 2 , or alkylamino, including esters, amides, and salts thereof; and W is C(O), C(S), S(O), or SO 2 . Optionally, R 5 and R 6 , together with the N—W bond of formula (I), comprise a macrocyclic ring.

  本发明提供了一种测定突变复制生物实体中生化物种与其前体相比的生化适应性的测定方法。本发明还提供了一种连续荧光测定法，用于测量蛋白酶抑制剂的抗HIV蛋白酶活性。本发明还提供了一种用于减少药物耐药性出现的治疗性化合物的给药方法。本发明还提供了一种式（I）的化合物或其药学上可接受的盐、前药、组合物或酯，其中A是式（A）、（B）、（C）或（D）的一种；R1、R2、R3、R5或R6为H，或者是一个可选的取代和/或含杂原子的烷基、烯基、炔基或环状基团；Y和/或Z为CH2、O、S、SO、SO2、氨基、酰胺、氨基甲酸酯、脲或其硫代衍生物，可选地用烷基、烯基或炔基基团取代；n为1到5；X为键、可选的取代亚甲基或乙烯基、氨基、O或S；Q为C（O）、C（S）或SO2；m为0到6；R4为OH、═O（酮）、NH2或烷基氨基，包括其酯、酰胺和盐；W为C（O）、C（S）、S（O）或SO2。可选地，R5和R6与式（I）的N-W键一起构成大环。
• Phospholipid-analogous compounds
  申请人：——

  公开号：US20030198663A1

  公开（公告）日：2003-10-23

  Phospholipid-analogous compounds of the general formula (I) 1 in which A 2 where R 1 and R 2 are, independently of one another, hydrogen, a saturated or unsaturated acyl or alkyl radical which can optionally be branched or/and substituted, where the total of the carbon atoms in the acyl and alkyl is 16 to 44 C atoms, s is an integer from 0 to 8, c is a radical of a primary or secondary alcohol of the formula RO—, where R is a saturated or unsaturated alkyl radical, mainly with cis double bond, of from 12 to 30 carbon atoms, n is an integer from 2 to 8, R 3 a can be 1,2-dihydroxypropyl or b can be alkyl with 1 to 3 C atoms when z is >0 or c can be alkyl with 1 to 3 carbon atoms when n≠2 and z=0, m is 1 or 2, x is an integer from 0 to 8, y is 1 for z=1 to 5 or is 1 to 4 for z=1 z is an integer from 0 to 5, are novel and are suitable as liposome constituents, solubilizers and pharmaceuticals.

  通式（I）的类磷脂类似化合物，其中A是一个基团，R1和R2独立地是氢、饱和或不饱和的酰基或烷基基团，可以是支链的和/或取代的，酰基和烷基中的碳原子总数为16到44个，s是从0到8的整数，c是具有RO—式的一级或二级醇基团，其中R是饱和或不饱和的烷基基团，主要带有顺式双键，碳原子数为12到30个，n是从2到8的整数，R3a可以是1,2-二羟基丙基或者当z>0时可以是碳原子数为1到3的烷基，或者当n≠2且z=0时可以是碳原子数为1到3的烷基，m为1或2，x是从0到8的整数，y对于z=1到5时为1，对于z=1时为1到4，z是从0到5的整数。这些化合物是新颖的，适用于脂质体成分、溶剂和药物。
• Fitness assay and associated methods
  申请人：Erickson W. John

  公开号：US20050158713A1

  公开（公告）日：2005-07-21

  The present invention provides an assay for determining the biochemical fitness of a biochemical species in a mutant replicating biological entity relative to its predecessor. The present invention further provides a continuous fluorogenic assay for measuring the anti-HIV protease activity of a protease inhibitor. The present invention also provides a method of administering a therapeutic compound that reduces the chances of the emergence of drug resistance in therapy. The present invention also provides a compound of the formula: or a pharmaceutically acceptable salt, a prodrug, a composition, or an ester thereof, wherein A is a group of the formula: R 1 , R 2 , R 3 , R 5 , or R 6 is H, or an optionally substituted and/or heteroatom-bearing alkyl, alkenyl, alkynyl, or cyclic group; Y and/or Z are CH 2 , O, S, SO, SO 2 , amino, amides, carbamates, ureas, or thiocarbonyl derivatives thereof, optionally substituted with an alkyl, alkenyl, or alkynyl group; n is from 1 to 5; X is a bond, an optionally substituted methylene or ethylene, an amino, 0 or S; Q is C(O), C(S), or SO 2 ; m is from 0 to 6; R 4 is OH, ═O (keto), NH 2 , or alkylamino, including esters, amides, and salts thereof; and W is C(O), C(S), S(O), or SO 2 . Optionally, R 5 and R 6 , together with the N—W bond of formula (I), comprise a macrocyclic ring.

  本发明提供了一种用于确定突变复制生物实体中生化种类的生化适应性的测定方法，相对于其前身。本发明还提供了一种连续荧光测定法，用于测量蛋白酶抑制剂的抗HIV蛋白酶活性。本发明还提供了一种用于给予治疗化合物的方法，该化合物减少了在治疗中出现药物耐受性的机会。本发明还提供了以下化合物：或其药学上可接受的盐，前药，组合物或酯，其中A是以下公式的基团：R1、R2、R3、R5或R6是H，或者是一个可选地取代和/或杂原子承载的烷基，烯基，炔基或环状基团; Y和/或Z是CH2、O、S、SO、SO2、氨基、酰胺、氨基甲酸酯、脲或其硫代衍生物，可选地取代烷基，烯基或炔基; n为1至5; X是键，可选地取代的亚甲基或乙烯基，氨基，0或S; Q为C（O），C（S）或SO2; m为0至6; R4为OH，═O（酮），NH2或烷基氨基，包括其酯，酰胺和盐; W为C（O），C（S），S（O）或SO2。可选地，R5和R6与公式（I）的N-W键一起包括一个大环状环。
• PHOSPHOLIPID-ANALOGOUS COMPOUNDS
  申请人：EIBL Hans-Jörg

  公开号：US20100183705A1

  公开（公告）日：2010-07-22

  Phospholipid-analogous compounds of the general formula (I) in which A where R 1 and R 2 are, independently of one another, hydrogen, a saturated or unsaturated acyl or alkyl radical which can optionally be branched or/and substituted, where the total of the carbon atoms in the acyl and alkyl is 16 to 44 C atoms, s is an integer from 0 to 8, c is a radical of a primary or secondary alcohol of the formula RO—, where R is a saturated or unsaturated alkyl radical, mainly with cis double bond, of from 12 to 30 carbon atoms, n is an integer from 2 to 8, R 3 a can be 1,2-dihydroxypropyl or b can be alkyl with 1 to 3 C atoms when z is >0 or c can be alkyl with 1 to 3 carbon atoms when n≠2 and z=0, m is 1 or 2, x is an integer from 0 to 8, y is 1 for z=1 to S′ or is 1 to 4 for z=1 z is an integer from 0 to 5, are novel and are suitable as liposome constituents, solubilizers and pharmaceuticals.

  通式（I）的类磷脂衍生物，其中A是，R1和R2分别是氢，饱和或不饱和的脂肪酰基或烷基，可以选择支链或/和取代，其中酰基和烷基中的碳原子总数为16到44个碳原子，s是0到8的整数，c是RO—的主要为顺式双键的一级或二级醇的基团，其中R是饱和或不饱和的烷基基团，其碳原子数为12到30个，n是2到8的整数，R3a可以是1,2-二羟基丙基或当z>0时可以是1到3个C原子的烷基，或当n≠2且z=0时可以是1到3个碳原子的烷基，m为1或2，x是0到8的整数，y为z=1到S'时为1或z=1z时为1到4，z是0到5的整数，这些化合物是新的，并适用于作为脂质体成分，溶解剂和药物。