4-t-butyldimethylsiloxy-2,3-epoxycyclopentan-1-one | 64079-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-t-butyldimethylsiloxy-2,3-epoxycyclopentan-1-one
• 英文别名: (R)-4-(tert-Butyldimethylsilanyloxy)-6-oxabicyclo[3.1.0]hexan-2-one；4(RS)-t-butyldimethylsilyloxy-2,3-epoxycyclopentanone；4-[tert-butyl(dimethyl)silyl]oxy-6-oxabicyclo[3.1.0]hexan-2-one
• CAS: 64079-55-6
• 化学式: C₁₁H₂₀O₃Si
• 分子量: 228.363
• InChiKey: KFTKJPWFFSOXRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-t-butyldimethylsiloxy-2,3-epoxycyclopentan-1-one 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 cerium(III) chloride 作用下， 生成 3-chloro-4-tert-butyldimethylsilyloxy-2-cyclopentenone
  参考文献：
  名称：

  Synthesis of new antineoplastic alkylidenecyclopentenones.

  摘要：

  新型共轭环戊烯酮，5-烷基烯基-4-羟基-2-环戊烯酮（3）和5-烷基烯基-2-氯-4-羟基-2-环戊烯酮（4），是通过两种不同的路径从4-叔丁基二甲基硅氧基-2-环戊烯酮（5）合成的。这些新化合物及其合成中间体在体外强烈抑制L1210肿瘤细胞的生长。

  DOI：

  10.1248/cpb.33.4120
• 作为产物：
  描述：

  (4R)-(+)-T-丁基二甲基硅氧-1-酮 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 生成 4-t-butyldimethylsiloxy-2,3-epoxycyclopentan-1-one
  参考文献：
  名称：

  3, 7 or 3 and 7 thia or oxa prostanoic acid derivatives as agents for lowering intraocular pressure

  摘要：

  本发明提供了一种治疗眼压增高或青光眼的方法，包括向患有眼压增高或青光眼的动物施用一定治疗剂量的一种化合物，该化合物由一般式I表示；其中A、B、D、X、Y、Z、R1、R3和R4如规范中定义。

  公开号：

  US06538018B1

文献信息

• 3, 7 or 3 and 7 thia or oxa prostanoic acid derivatives as agents for lowering intraocular pressure
  申请人：Allergan, Inc.

  公开号：US06538018B1

  公开（公告）日：2003-03-25

  The present invention provides a method of treating ocular hypertension or glaucoma which comprises administering to an animal having ocular hypertension or glaucoma therapeutically effective amount of a compound represented by the general formula I; where in A, B, D, X, Y, Z, R1, R3 and R4 are as defined in the specification.

  本发明提供了一种治疗眼压增高或青光眼的方法，包括向患有眼压增高或青光眼的动物施用一定治疗剂量的一种化合物，该化合物由一般式I表示；其中A、B、D、X、Y、Z、R1、R3和R4如规范中定义。
• Synthesis of 7-thiaprostaglandin E1 congeners: Potent inhibitors of platelet aggregation.
  作者：TOSHIO TANAKA、NORIAKI OKAMURA、KIYOSHI BANNAI、ATSUO HAZATO、SATOSHI SUGIURA、KENJI MANABE、FUKUYOSHI KAMIMOTO、SEIZI KUROZUMI

  DOI：10.1248/cpb.33.2359

  日期：——

  Novel 7-thiaprostaglandin E1 derivatives and congeners were synthesized by a stepwise three-component coupling process, which involves the introduction of α-side chains (thiols) and β-side chains (organocopper reagents) into (R)-4-tert-butyldimethylsilyloxy-2-cyclopentenone. Several acid derivatives of 7-thiaprostaglandin E1 were also prepared either by enzymatic or by chemical methods. The stereochemistry of these products was assigned on the basis of the results with chiral protected cyclopentenones and chiral ω-side chains. Some of these 7-thiaprostaglandin E1 congeners were found to exhibit more potent platelet aggregation-inhibitory activity than PGE1. The structure-activity relationship of these congeners is discussed.

  合成了一系列新型的7-硫前列腺素E1衍生物和同系物，采用一步法的三组分耦合过程，该过程涉及向(R)-4-叔丁基二甲基硅氧基-2-环戊烯酮引入α侧链（硫醇）和β侧链（有机铜试剂）。还通过酶法或化学方法制备了几种7-硫前列腺素E1的酸衍生物。这些产物的立体化学基于对手性保护的环戊烯酮和手性ω侧链的结果进行分配。发现某些7-硫前列腺素E1同系物的血小板聚集抑制活性比PGE1更强。文中讨论了这些同系物的结构-活性关系。
• 3, 7or3 and 7 thia or oxa prostanoic acid derivatives as agents for lowering intraocular pressure
  申请人：Allergan Sales, Inc.

  公开号：US20030027853A1

  公开（公告）日：2003-02-06

  The present invention provides a method of treating ocular hypertension or glaucoma which comprises administering to an animal having ocular hypertension or glaucoma therapeutically effective amount of a compound represented by the general formula I; 1 wherein hatched lines represent the &agr; configuration, a triangle represents the &bgr; configuration, a wavy line represents the &agr; configuration or the &bgr; configuration and a dotted line represents the presence or absence of a double bond; A and B are independently selected from the group consisting of O, S and CH 2 ; provided that at least one of A or B is S; D represents a covalent bond or CH 2 , O, S or NH; X is CO 2 R, CONR 2 , CH 2 OR, P(O)(OR) 2 , CONRSO 2 R SONR 2 or 2 Y is O, OH, OCOR 2 , halogen or cyano; Z is CH 2 or a covalent bond; R is H, or R 2 ; R 1 is H, R 2 , phenyl, or COR 2 ; R 2 is C 1 -C 5 lower alkyl or alkenyl and R 3 is benzothienyl, benzofuranyl, naphthyl or substituted derivatives thereof, wherein the substituents maybe selected from the group consisting of C 1 -C 5 alkyl, halogen, CF 3 , CN, NO 2 , NR 2 , CO 2 R and OR.

  本发明提供了一种治疗眼压增高或青光眼的方法，包括向患有眼压增高或青光眼的动物施用一定疗效量的一种化合物，其表示为通用公式I；其中，斜线代表α构型，三角形代表β构型，波浪线代表α构型或β构型，虚线代表双键的存在或不存在；A和B分别选择自O、S和CH2的组合；至少A或B中的一个是S；D代表共价键或CH2、O、S或NH；X为CO2R、CONR2、CH2OR、P(O)(OR)2、CONRSO2R、SONR2或2；Y为O、OH、OCOR2、卤素或氰基；Z为CH2或共价键；R为H或R2；R1为H、R2、苯基或COR2；R2为C1-C5低碳烷基或烯烃基，R3为苯并噻吩基、苯并呋喃基、萘基或其取代衍生物，其中取代基可选择自C1-C5烷基、卤素、CF3、CN、NO2、NR2、CO2R和OR的组合。
• 3,7 or 3 and 7 thia or oxa prostanoic acid derivatives as agents for lowering intraocular pressure
  申请人：Allergan Sales, Inc.

  公开号：US06410591B1

  公开（公告）日：2002-06-25

  The present invention provides a method of treating ocular hypertension or glaucoma which comprises administering to an animal having ocular hypertension or glaucoma a therapeutically effective amount of a 3, 7 or 3 and 7 thia or oxa prostanoic acid derivative.

  本发明提供了一种治疗眼压升高或青光眼的方法，包括向患有眼压升高或青光眼的动物施用治疗有效量的3、7或3和7硫或氧代前列腺酸衍生物。
• 2-Organothio-2-cyclopentenones, organothio-cyclopentanes derived
  申请人：Teijin Limited

  公开号：US04180672A1

  公开（公告）日：1979-12-25

  Organothiocyclopentanes of the formula ##STR1## wherein E represents >C.dbd.O or ##STR2## in which Z' represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; X represents --S--, --CH.sub.2 --, --CH.dbd.; represents a single or double bond; R' represents a monovalent or divalent organic group containing 1 to 25 carbon atoms; R represents a monovalent organic group containing 1 to 25 carbon atoms; Z represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; and when both E and Z represent a hydroxyl group or a protected hydroxyl group, X represents --S--. Also, 2-organothio-2-cyclopentenones of the formula ##STR3## wherein R and Z are as defined above. The compounds of formula (I) are prepared by reacting 2,3-epoxy-cyclopentanone or its derivatives with mercaptans in the presence of basic compounds. The compounds of formula (II) are prepared by reacting the compounds of formula (I) with mercaptans or organocopper-lithium compounds, and optionally reducing the resulting products, and optionally protecting the hydroxyl group at their cyclopentane ring. The compounds of formula (I) have an action of inhibiting ulcer formation, and are useful intermediates for the compounds of formula (II). The compounds of formula (II) are monothia- or dithia-prostanoic acid derivatives, and exhibit various superior pharmacological actions.

  公式为##STR1##的有机硫代环戊烷，其中E代表>C.dbd.O或##STR2##，其中Z'代表氢原子、羟基或受保护的羟基；X代表--S--、--CH.sub.2--、--CH.dbd.--；代表单键或双键；R'代表含有1至25个碳原子的一价或二价有机基团；R代表含有1至25个碳原子的一价有机基团；Z代表氢原子、羟基或受保护的羟基；当E和Z均代表羟基或受保护的羟基时，X代表--S--。此外，公式为##STR3##的2-有机硫代-2-环戊烯酮，其中R和Z如上定义。通过将2,3-环氧-环戊酮或其衍生物与巯基化合物在碱性化合物存在下反应制备公式(I)的化合物。通过将公式(I)的化合物与巯基化合物或有机铜锂化合物反应，并可选择性地还原所得产物，并可选择性地保护其环戊烷环上的羟基来制备公式(II)的化合物。公式(I)的化合物具有抑制溃疡形成的作用，并可用作公式(II)的化合物的有用中间体。公式(II)的化合物是单硫代或二硫代前列腺酸衍生物，并表现出各种优越的药理作用。