methyl (R)-3-tetrahydropyranyloxybutanoate | 77234-51-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (R)-3-tetrahydropyranyloxybutanoate
• 英文别名: methyl (3R)-3-(oxan-2-yloxy)butanoate
• CAS: 77234-51-6
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: NNHKCBGPBCBNSG-HNHGDDPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-3-tetrahydropyranyloxybutanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (R)-3-((tetrahydro-2H-pyran-2-yl)oxy)butan-1-ol
  参考文献：
  名称：

  钴催化的烷基甲苯磺酸盐和二烯的羰基化交叉偶联：低压下二烯的立体定向合成

  摘要：

  尽管烷基亲电子试剂的有机金属交叉偶联取得了进展，但手性非外消旋底物的立体选择性反应很少。在本文中，我们报道了烷基对甲苯磺酸酯和二烯产生对映体富集的二烯酮的立体有择的羰基化偶联。该催化过程使用简单的钴催化剂在低压和温和条件下进行，并扩展到各种甲苯磺酸酯和二烯偶联伙伴。该转化构成了一种独特的，收敛的方法，可以从易于获取的起始原料中不对称地合成有价值的羰基化合物。

  DOI：

  10.1021/jacs.7b07983
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 (R)-3-羟基丁酸甲酯 在 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 生成 methyl (R)-3-tetrahydropyranyloxybutanoate
  参考文献：
  名称：

  钴催化的烷基甲苯磺酸盐和二烯的羰基化交叉偶联：低压下二烯的立体定向合成

  摘要：

  尽管烷基亲电子试剂的有机金属交叉偶联取得了进展，但手性非外消旋底物的立体选择性反应很少。在本文中，我们报道了烷基对甲苯磺酸酯和二烯产生对映体富集的二烯酮的立体有择的羰基化偶联。该催化过程使用简单的钴催化剂在低压和温和条件下进行，并扩展到各种甲苯磺酸酯和二烯偶联伙伴。该转化构成了一种独特的，收敛的方法，可以从易于获取的起始原料中不对称地合成有价值的羰基化合物。

  DOI：

  10.1021/jacs.7b07983

文献信息

• Manganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates
  作者：Hannah Shenouda、Erik J. Alexanian

  DOI：10.1021/acs.orglett.9b03706

  日期：2019.11.15

  The development of a stereospecific hydroxymethylation of alkyl tosylates using an inexpensive, first-row catalyst is described. The transformation proceeds under mild conditions with low pressure to deliver homologated alcohols as products. Chiral, nonracemic β-branched primary alcohols are obtained with high enantiospecificity from easily accessed secondary alkyl substrates. Simple modification of

  描述了使用便宜的第一行催化剂开发烷基甲苯磺酸酯的立体有针对性的羟甲基化。该转化在温和条件下以低压进行，以递送作为产物的同系醇。从容易获得的仲烷基底物上获得具有高对映体特异性的手性，非外消旋的β-支链伯醇。将反应体系的简单修改还允许访问α- ð 2醇。这些研究使用阴离子金属羰基催化，以从一氧化碳中获得具有挑战性的羟甲基阴离子的合成等价物。
• [EN] MACROCYCLIC LRRK2 KINASE INHIBITORS<br/>[FR] INHIBITEURS MACROCYCLIQUES DE LA KINASE LRRK2
  申请人：SERVIER LAB

  公开号：WO2022194976A1

  公开（公告）日：2022-09-22

  Compounds of formula (I) are useful as LRRK2 kinase inhibitors.

  式(I)的化合物可用作LRRK2激酶抑制剂。
• Synthesis of 16-membered-ring macrolide antibiotics. 4. Carbomycin B and leucomycin A3: total synthesis of cyclic key intermediate
  作者：K. C. Nicolaou、M. R. Pavia、S. P. Seitz

  DOI：10.1021/ja00395a044

  日期：1981.3
• Asymmetric Addition of an Electrophile to Naphthalenes Promoted and Stereodirected by Alcohol
  作者：Morifumi Fujita、Hironori Matsushima、Takashi Sugimura、Akira Tai、Tadashi Okuyama

  DOI：10.1021/ja0029477

  日期：2001.4.1

  4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) reacts with 1 -methoxy-4-methylnaphthalene to give the 1,4-addition product in the presence of methanol; the reaction does not proceed in the absence of the alcohol. Methoxy exchange (with CD3OD) was also observed during the reaction. Reactions of PTAD with 1-(3-hydroxypropoxy)-4-methylnaphthalene and related naphthalenes afford stereoselectively 1,4-adducts (70-98% of the major diastereomer). The stereoface-selective addition of PTAD at C-4 with concurrent formation of an acetal at C-1 takes place in a syn manner, which is induced by the hydrogen-bonding interaction between PTAD and the hydroxy group. The alpha -methyl substitution on the propoxy side chain strongly enhances the stereodifferentiation (90% de) and accelerates the cyclization by the Thorpe-Ingold effect. The alkoxy moiety of the adduct is easily removed to give 4-methyl-4-amino-4H-naphthalen-1-one with high enantiomeric excess. The gamma -methyl group of the side chain also affects the stereodifferentiation. Thus, the two stereogenic centers of the (1S,3R)-3-hydroxy-1-methylbutoxy side chain work together to achieve the high stereodifferentiating 1,4-addition from the Si-Re face (up to 96% ee). Epimerization of the cyclic acetal of a minor adduct was observed during the reaction of 1-(3-hydroxybutoxy)-4-methylnaphthalene, indicating that the minor component of the final products is derived from the initial minor syn adduct formed from the opposite face. The syn selectivity of the addition is achieved completely in the initial stage of formation of both the major and the minor adducts.
• Yuasa, Yoko; Ando, Jun; Shibuya, Shiroshi, Journal of the Chemical Society. Perkin transactions I, 1996, # 5, p. 465 - 473
  作者：Yuasa, Yoko、Ando, Jun、Shibuya, Shiroshi

  DOI：——

  日期：——