3exo-Methyl-8-oxabicyclo<3.2.1>oct-6-en-3endo-ol | 127617-38-3

• 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: 3exo-Methyl-8-oxabicyclo<3.2.1>oct-6-en-3endo-ol
• 英文别名: (1R,3S,5S)-3-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-ol
• CAS: 127617-38-3；76400-42-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: BRJQVMNTAPIFBP-JIGDXULJSA-N

物化性质

• 沸点：
  240.3±40.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3exo-Methyl-8-oxabicyclo<3.2.1>oct-6-en-3endo-ol 在 sodium tetrahydroborate 、 mercury(II) diacetate 作用下， 生成 1-Methyl-2,6-dioxatricyclo<3.3.1.0^3,7>nonan
  参考文献：
  名称：

  杂三环癸烷XXVII。Ein weiterer Zugang zu 2,6-Dioxatricyclo [3.3.2.0 3,7 ] decan †

  摘要：

  2,6-二氧杂三环[3.3.2.0 3,7 ]癸烷的另一种方法

  DOI：

  10.1002/hlca.19800630611
• 作为产物：
  描述：

  Spiro<(8-oxabicyclo<3.2.1>oct-6-en)-3,2'-(1'endo)oxiran> 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.08h， 以83%的产率得到3exo-Methyl-8-oxabicyclo<3.2.1>oct-6-en-3endo-ol
  参考文献：
  名称：

  杂三环癸烷XXVII。Ein weiterer Zugang zu 2,6-Dioxatricyclo [3.3.2.0 3,7 ] decan †

  摘要：

  2,6-二氧杂三环[3.3.2.0 3,7 ]癸烷的另一种方法

  DOI：

  10.1002/hlca.19800630611

文献信息

• PROCESS FOR THE PREPARATION OF C-FMS KINASE INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：US20140045789A1

  公开（公告）日：2014-02-13

  The present invention is directed to a process for the preparation of heterocyclic derivatives of formula I wherein J, X, Z, and R 2 are as defined herein. Such compounds are useful as protein tyrosine kinase inhibitors, more particularly inhibitors of c-fms kinase.

  本发明涉及一种用于制备公式I的杂环衍生物的方法，其中J、X、Z和R2如本文所定义。这些化合物可用作蛋白酪氨酸激酶抑制剂，更具体地说是c-fms激酶的抑制剂。
• Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM)
  作者：Dennis G. Gillingham、Osamu Kataoka、Steven B. Garber、Amir H. Hoveyda

  DOI：10.1021/ja0458672

  日期：2004.10.1

  efficient method for enantioselective synthesis of highly functionalized pyrans (up to 98% ee) through Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis is described. Reactions are promoted by a recyclable chiral Ru-chloride or a new chiral Ru-iodide complex; the latter catalyst is less efficient but gives rise to significantly higher levels of enantioselectivity. Catalytic reactions can be

  描述了一种通过 Ru 催化的不对称开环复分解/交叉复分解反应对映选择性合成高度官能化吡喃（高达 98% ee）的有效方法。反应由可回收的手性氯化钌或新的手性碘化钌配合物促进；后一种催化剂效率较低，但产生了显着更高水平的对映选择性。催化反应可以在未蒸馏的溶剂中进行，并且可以使用多种底物，包括那些含有仲醇和叔醇的底物。还介绍了突出催化方法效用的代表性区域选择性功能化。
• <i>Z</i>- and Enantioselective Ring-Opening/Cross-Metathesis with Enol Ethers Catalyzed by Stereogenic-at-Ru Carbenes: Reactivity, Selectivity, and Curtin–Hammett Kinetics
  作者：R. Kashif M. Khan、Robert V. O’Brien、Sebastian Torker、Bo Li、Amir H. Hoveyda

  DOI：10.1021/ja304827a

  日期：2012.8.1

  The first instances of Z- and enantioselective Ru-catalyzed olefin metathesis are presented. Ring-opening/cross-metathesis (ROCM) reactions of oxabicyclic alkenes and enol ethers and a phenyl vinyl sulfide are promoted by 0.5-5.0 mol % of enantiomerically pure stereogenic-at-Ru complexes with an aryloxy chelate tethered to the N-heterocyclic carbene. Products are formed efficiently and with exceptional

  介绍了 Z 和对映选择性 Ru 催化的烯烃复分解的第一个实例。0.5-5.0 mol % 的对映异构纯立体 Ru 配合物与连接在 N-杂环卡宾上的芳氧基螯合物促进了氧杂双环烯烃和烯醇醚与苯基乙烯基硫化物的开环/交叉复分解 (ROCM) 反应. 产品可高效形成且具有出色的对映选择性（> 98:2 对映异构体比）。令人惊讶的是，对映选择性 ROCM 反应以高 Z 选择性（高达 98% Z）进行。此外，反应以与芳基烯烃相反的对映选择性进行，芳基烯烃仅提供 E 异构体。提供了支持 Curtin-Hammett 动力学的初步 DFT 计算以及解释立体选择性水平和趋势的初始模型。
• Ring-opening reactions of an oxabicyclic compound with cuprates
  作者：Mark Lautens、Carlo Di Felice、Alexandre Huboux

  DOI：10.1016/s0040-4039(01)93360-x

  日期：1989.1

  The ring-opening reaction of 8-oxabicyclic[3.2.1]oct-6-en-3-one with cuprates is described. SN2′ attack is the predominant pathway giving rise to products isomeric to those derived from opening of vinylepoxides under similar conditions.

  描述了8-氧杂双环[3.2.1] oct-6-en-3-one与铜酸盐的开环反应。S N 2'攻击是主要途径，其产生的产物与在相似条件下从乙烯基环氧化合物的打开衍生而来的产物同分异构。
• INHIBITORS OF C-FMS KINASE
  申请人：Janssen Pharmaceutica N.V.

  公开号：EP3208269A1

  公开（公告）日：2017-08-23

  The invention is directed to compounds of Formula I: wherein Z, X, J, R2 and W are set forth in the specification, as well as solvates, hydrates, tautomers and pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase. Methods of treating autoimmune diseases; and diseases with an inflammatory component; treating metastasis from ovarian cancer, uterine cancer, breast cancer, prostate cancer, lung cancer, colon cancer, stomach cancer, hairy cell leukemia; and treating pain, including skeletal pain caused by tumor metastasis or osteoarthritis, or visceral, inflammatory, and neurogenic pain; as well as osteoporosis, Paget's disease, and other diseases in which bone resorption mediates morbidity including rheumatoid arthritis, and other forms of inflammatory arthritis, osteoarthritis, prosthesis failure, osteolytic sarcoma, myeloma, and tumor metastasis to bone with the compounds of Formula I, are also provided.

  本发明涉及式 I 的化合物： 其中Z、X、J、R2和W如说明书所述，以及它们的溶解物、水合物、同系物和药学上可接受的盐，可抑制蛋白酪氨酸激酶，特别是c-fms激酶。治疗自身免疫性疾病的方法；治疗具有炎症成分的疾病的方法；治疗卵巢癌、子宫癌、乳腺癌、前列腺癌、肺癌、结肠癌、胃癌、毛细胞白血病转移的方法；治疗疼痛的方法，包括肿瘤转移或骨关节炎引起的骨骼疼痛，或内脏疼痛、炎症疼痛和神经源性疼痛；以及骨质疏松症、Paget's 病和其他骨吸收介导发病的疾病，包括类风湿性关节炎和其他形式的炎症性关节炎、骨关节炎、假体失效、溶骨肉瘤、骨髓瘤和肿瘤骨转移。