(2R,3S)-(3-phenyloxiran-2-yl)methanol | 21915-53-7

• 物质功能分类: 化学试剂 - 有机试剂 - 醚类
• 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: (2R,3S)-(3-phenyloxiran-2-yl)methanol
• 英文别名: ((2R,3S)-3-phenyloxiran-2-yl)methanol；(2R,3S)-2,3-epoxy-3-phenylpropan-1-ol；(2R,3S)-2,3-epoxy-3-phenylpropanol；(2R,3S)-3-phenyloxiranemethanol；S,S-3-phenylglycidol；phenylglycidol；(2R,3R)-3-Phenylglycidol；[(2R,3S)-3-phenyloxiran-2-yl]methanol
• CAS: 21915-53-7；40641-81-4；98819-67-1；98819-68-2；99528-63-9；104196-23-8；105663-44-3；116661-35-9；91465-28-0
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: PVALSANGMFRTQM-BDAKNGLRSA-N

物化性质

• 熔点：
  52-55 °C
• 沸点：
  231.72°C (rough estimate)
• 密度：
  1.0858 (rough estimate)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P201,P202,P210,P261,P264,P271,P280,P302+P352+P312,P305+P351+P338,P308+P313,P337+P313,P370+P378,P403+P233,P405,P501
• 危险品运输编号：
  2810
• 危险性描述：
  H227,H302,H312,H315,H319,H350

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(3-phenyloxiran-2-yl)methanol 在 咪唑 、 草酰氯 、 四丁基氟化铵 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 44.0h， 生成 (4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-goniotriol and (+)-goniofufurone

  摘要：

  The Enantioselective synthesis of two antitumor styryl lactones, (+)-goniotriol and (+)-goniofufurone, have been completed starting from cinnamyl alcohol in ten and eleven steps with an overall yield of 21% and 12%, respectively.

  DOI：

  10.1016/0040-4020(94)01025-u
• 作为产物：
  描述：

  3-苯基丙-2-烯-1-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(2R,3S)-(3-phenyloxiran-2-yl)methanol
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-goniotriol and (+)-goniofufurone

  摘要：

  The Enantioselective synthesis of two antitumor styryl lactones, (+)-goniotriol and (+)-goniofufurone, have been completed starting from cinnamyl alcohol in ten and eleven steps with an overall yield of 21% and 12%, respectively.

  DOI：

  10.1016/0040-4020(94)01025-u

文献信息

• [EN] 3-ARYLOXY/ THIO-2, 3-SUBSTITUTED PROPANAMINES AND THEIR USE IN INHIBITING SEROTONIN AND NOREPINEPHRINE REUPTAKE<br/>[FR] 3-ARYLOXY/THIO-2, 3-SUBSTITUE PROPANAMINES ET LEUR UTILISATION POUR INHIBER LE RECAPTAGE DE LA SEROTONINE ET DE LA NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2004043903A1

  公开（公告）日：2004-05-27

  There is provided a compound of formula (I) wherein A is selected from -O- and -S-; X is selected from phenyl optionally substituted with up to 5 substituents each independently selected from halo, C1-C4 alkyl and C1-C4 alkoxy, thienyl optionally substituted with up to 3 substituents each independently selected from halo and C1-C4 alkyl, and C2-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl and C4-C8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, -CF3, -CN and -CONH2; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3-benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, up to 5 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, nitro, acetyl, -CF3, -SCF3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; Z is selected from OR3 or F, wherein R3 is selected from H, C1-C6 alkyl and phenyl C1-C6 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereofwith the proviso that when Y is optionally substituted phenyl or optionally substituted 1,3-benzodioxolyl and Z is OR3 and X is optionally substituted phenyl then A is -S-.

  提供一种化合物，其化学式为（I），其中A从-O-和-S-中选择；X从苯基选项地取代，每个取代基可独立地从卤素、C1-C4烷基和C1-C4烷氧基中选择最多5个取代基，噻吩基选项地取代，每个取代基可独立地从卤素和C1-C4烷基中选择最多3个取代基，以及C2-C8烷基、C2-C8烯基、C3-C8环烷基和C4-C8环烷基烷基，每个基可选地取代，每个取代基可独立地从卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷基-S(O)n-（其中n为0、1或2）、-CF3、-CN和-CONH2中选择；Y从苯基、萘基、二氢苯并噻吩基、苯并噻唑基、苯并异噻唑基、喹啉基、异喹啉基、萘啉基、噻吩吡啉基、茚基、1,3-苯并二氧杂环戊基、苯并噻吩基、吲哚基和苯并呋喃基中选择，每个基可选地取代，最多可独立地从卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷基-S(O)n-（其中n为0、1或2）、硝基、乙酰基、-CF3、-SCF3和氰基中选择最多4个或在可能的情况下最多5个取代基；当Y为吲哚基时，它可以被取代或进一步被N-取代基取代，N-取代基从C1-C4烷基中选择；Z从OR3或F中选择，其中R3从H、C1-C6烷基和苯基C1-C6烷基中选择；R1和R2各自独立地为H或C1-C4烷基；以及其药学上可接受的盐，但有一个条件，即当Y为可选地取代的苯基或可选地取代的1,3-苯并二氧杂环戊基，Z为OR3且X为可选地取代的苯基时，A为-S-。
• A Diacetate Ketone-Catalyzed Asymmetric Epoxidation of Olefins
  作者：Bin Wang、Xin-Yan Wu、O. Andrea Wong、Brian Nettles、Mei-Xin Zhao、Dajun Chen、Yian Shi

  DOI：10.1021/jo900330n

  日期：2009.5.15

  A fructose-derived diacetate ketone has been shown to be an effective catalyst for asymmetric epoxidation. High ee values have been obtained for a variety of trans and trisubstituted olefins including electron-deficient α,β-unsaturated esters as well as certain cis olefins.

  果糖衍生的二乙酸酮已被证明是不对称环氧化的有效催化剂。各种反式和三取代烯烃（包括缺电子 α,β-不饱和酯以及某些顺式烯烃）都获得了高 ee 值。
• Asymmetric Epoxidation of Allylic Alcohols Catalyzed by Vanadium–Binaphthylbishydroxamic Acid Complex
  作者：Masahiro Noji、Toshihiro Kobayashi、Yuria Uechi、Asami Kikuchi、Hisako Kondo、Shigeo Sugiyama、Keitaro Ishii

  DOI：10.1021/acs.joc.5b00185

  日期：2015.3.20

  acid (BBHA) complex-catalyzed asymmetric epoxidation of allylic alcohols is described. The optically active binaphthyl-based ligands BBHA 2a and 2b were synthesized from (S)-1,1′-binaphthyl-2,2′-dicarboxylic acid and N-substituted-O-trimethylsilyl (TMS)-protected hydroxylamines via a one-pot, three-step procedure. The epoxidations of 2,3,3-trisubstituted allylic alcohols using the vanadium complex of

  描述了钒-联萘基双异羟肟酸（BBHA）络合物催化的烯丙醇不对称环氧化。由（S）-1,1'-联萘-2,2'-二羧酸和N-取代-O-三甲基甲硅烷基（TMS）-保护的羟胺通过单-羟基合成旋光的基于联萘的配体BBHA 2a和2b。锅，分三步操作。使用2a的钒配合物，在TBHP水溶液中轻松地进行使用2a的钒配合物进行的2,3,3-三取代的烯丙醇的环氧化，从而得到具有良好对映选择性的优良（2 R）-环氧醇。
• Bioresolution Production of (2R,3S)-Ethyl-3-phenylglycidate for Chemoenzymatic Synthesis of the Taxol C-13 Side Chain by Galactomyces geotrichum ZJUTZQ200, a New Epoxide-Hydrolase-Producing Strain
  作者：Chun Wei、Jinlong Ling、Honglei Shen、Qing Zhu

  DOI：10.3390/molecules19068067

  日期：——

  racemic ethyl 3-phenylglycidate (rac-EPG) for producing (2R,3S)-ethyl-3-phenylglycidate ((2R,3S)-EPG). G. geotrichum ZJUTZQ200 was verified to be able to afford high enantioselectivity in whole cell catalyzed synthesis of this chiral phenylglycidate synthon. After the optimization of the enzymatic production and bioresolution conditions, (2R,3S)-EPG was afforded with high enantioselectivity (e.e.S >

  新分离出的含有环氧化物水解酶的土霉半乳杆菌 ZJUTZQ200 菌株用于分解外消旋 3-苯基缩水甘油酸乙酯 (rac-EPG)，用于生产 (2R,3S)-3-苯基缩水甘油酸乙酯 ((2R,3S)-EPG)。G. geotrichum ZJUTZQ200 被证实能够在全细胞催化合成这种手性苯基缩水甘油酸合成子中提供高对映选择性。在优化酶促生产和生物拆分条件后，(2R,3S)-EPG 在反应 8 小时后具有高对映选择性（eeS > 99%，E > 49）。发现共溶剂、pH 缓冲溶液和底物/细胞比对 G. geotrichum ZJUTZQ200 的生物分辨率有显着影响。基于生物拆分产物 (2R,3S)-EPG，紫杉醇的侧链乙基 (2R,
• The reaction of dichlorocarbene with β-ethanolamines stereospecific synthesis of epoxides
  作者：Luís Castedo、José L. Castro、Ricardo Riguera

  DOI：10.1016/s0040-4039(01)91561-8

  日期：——

  Optically pure β-ethanolamines were converted into epoxides in good yield and with high e.e. ( ⩾, 95%) by reaction with dichlorocarbene. By this method α-aminoacids were successfully converted into synthetically useful epoxides.

  通过与二氯卡宾反应，将光学纯的β-乙醇胺以高收率和高ee（（，95％）转化为环氧化物。通过这种方法，α-氨基酸成功地转化为合成上有用的环氧化物。