(1S)-(-)-10-iodo-2-exobornanol | 183446-26-6

• 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)-(-)-10-iodo-2-exobornanol
• 英文别名: (1S,2R)-10-iodo-isoborneol；exo-2-hydroxy-10-bornyl iodide；(1S,2R,4R)-1-(iodomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 183446-26-6
• 化学式: C₁₀H₁₇IO
• 分子量: 280.149
• InChiKey: QBWSONVBKIJKFV-NQMVMOMDSA-N

物化性质

• 沸点：
  292.2±13.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S)-(-)-10-iodo-2-exobornanol 在 lithium sulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以51%的产率得到di-exo-2-hydroxy-10-bornyl sulfide
  参考文献：
  名称：

  Enantioselective Darzens reaction using organoselenide–lithium hydroxide complexes

  摘要：

  Asymmetric Darzens reaction catalyzed by chiral selenides is described. A novel Lewis acid/Bronsted base catalyst formed by C-2 symmetric chiral selenide-bearing isoborneol skeletons, which were readily prepared from (1S)-10-camphorsulfonic acid, and LiOH promoted the reaction of phenacyl bromide with aldehydes to afford the desired trans oxiranes with up to 62% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.082
• 作为产物：
  描述：

  D(+)-10-樟脑磺酸 在 lithium aluminium tetrahydride 、 碘 、 三苯基膦 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 19.0h， 生成 (1S)-(-)-10-iodo-2-exobornanol
  参考文献：
  名称：

  新型双齿莰烷磷烷配体的简洁前手性池方法

  摘要：

  双齿羟基磷烷 20 和磷烷次膦酸酯 21 分别带有莰烷骨架，分别由 (1S)-(+)-樟脑磺酸 8 和三乙基甲硅烷基通过五步和六步（产率 52% 和 28%）制备- 受保护的碘化物 17 作为关键中间体。获得了 21 的 X 射线晶体结构。

  DOI：

  10.1002/1099-0690(200012)2000:24<4119::aid-ejoc4119>3.0.co;2-x

文献信息

• Bidentate phosphorus ligands and their use in catalysis
  申请人：DEGUSSA AG

  公开号：US20020095049A1

  公开（公告）日：2002-07-18

  Chiral, unsymmetrical bidentate organophosphorus ligands of the formula (I) are reacted with transition metal centers to form complexes with catalytic activity. The compounds contain chiral bicycloaliphatic skeletons. Synthesis of the bidentate ligands proceeds from norbornyl derivatives. 1

  手性、非对称的双齿有机磷配体（化学式I）与过渡金属中心发生反应，形成具有催化活性的配合物。这些化合物包含手性的双环脂肪骨架。双齿配体的合成是从去莽烯衍生物开始进行的。
• Bidentate Organophosphorliganden und ihre Verwendung in der Katalyse
  申请人：Degussa Aktiengesellschaft

  公开号：EP1201673A1

  公开（公告）日：2002-05-02

  Diese Erfindung betrifft chirale, unsymmetrische bidentate Organophosphorliganden der Formel (I). Das Grundgerüst der erfindungsgemäßen Verbindungen besteht aus einem chiralen bicycloaliphatischen Grundgerüst.

  本发明涉及式（I）的手性不对称双叉有机磷配体。根据本发明的化合物的骨架由手性双环脂族骨架组成。
• Stereochemical Research on the Hydrolysis of Optically Pure Spirosulfuranes:  Efficient Synthesis of Chiral Sulfoxides with Completely Opposite Stereochemistry
  作者：Jian Zhang、Shinichi Saito、Toru Koizumi

  DOI：10.1021/jo981330t

  日期：1998.12.1

  The synthesis of optically pure alkoxy(acyloxy)spirosulfuranes 5a-e, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been developed in high yield and with excellent diastereoselectivity. The X-ray analyses of 5a and 5b indicated that the spirosulfuranes have the trigonal bipyramidal (TBP) structures around the sulfur atom. Recrystallization of 5c,d from moist solvent (95% EtOH aq) gave sulfoxides 7c,d, respectively, as single products with an S-s absolute configuration at the sulfur atom. In contrast, hydrolysis of sulfuranes 5b,c,d under the basic conditions afforded the sulfoxides 8b,c,d, with an R-s absolute configuration at the sulfur atom, in high yield and with excellent diastereoselectivity. The stereochemical and mechanistic study of the hydrolysis of spirosulfuranes was performed by using spirosulfurane 5a. Hydrolysis of 5a under acidic and basic conditions gave, diastereoselectively, the corresponding sulfoxides 7a and 8a with the opposite absolute configuration at the sulfur atom. The structures of the sulfoxides 7a,c and 8a,b were confirmed by X-ray crystallographic analyses. The mass spectral and O-17 NMR studies of the sulfoxides 7a-(18(17))O and 8a-(18(17))O, which were prepared by the hydrolysis of 5a with isotopically labeled water, revealed definitely that the oxygen atom bound to the sulfur atom in these compounds derives from water. The possible mechanisms of the reactions which account for the observed stereochemical results have been suggested.
• Diastereoselective Synthesis and Stereochemical Research of Optically Pure Telluronium Salts
  作者：Jian Zhang、Shinichi Saito、Toru Koizumi

  DOI：10.1021/jo9803131

  日期：1998.8.1

  The synthesis of optically pure telluronium salts 4a-i, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been achieved in high yield and selectivity by the reaction of chiral alkoxytelluranes 3a-i with organolithium and Grignard reagents. Both diastereoisomers of ethyl(2-exo-hydroxy-10-bornyl)methyltelluronium chloride (4a,b) and butyl(2-exo-hydroxy-10-bornyl)methyltelluronium chloride (4c,d) have been synthesized in optically pure form in high yield and with excellent diastereoselectivity. The method has been used for the asymmetric synthesis of chiral benzyl- and allyltelluronium salts 5a-h. Structures of these salts have been confirmed by X-ray analyses of 4a and 4b, which indicated that all of the salts have their pyramidal geometrical structures around the tellurium atom. The thermal and optical stability and the possible mechanisms of the reaction are also discussed.
• First synthesis and stereochemistry of enantiomerically pure spiroselenurane and spirotellurane using the 2-exo-hydroxy-10-bornyl group as a chiral ligand
  作者：Jian Zhang、Shigemasa Takahashi、Shinichi Saito、Toru Koizumi

  DOI：10.1016/s0957-4166(98)00352-8

  日期：1998.9

  The first synthesis of enantiomerically pure spiroselenuranes 8a-d and spirotelluranes 12a,b, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been developed and proceeds in good yield and with excellent diastereoselectivity. The X-ray analysis of spirotellurane 12a indicated that the spirochalcogenuranes have a trigonal bipyramidal (TBP) structure around the chalcogenium atom. A comparison of the spectroscopic properties of spirochalcogenuranes is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.