9-(2-hydroxyethyl)fluorene-9-carboxylic acid | 160254-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-(2-hydroxyethyl)fluorene-9-carboxylic acid
• CAS: 160254-96-6
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: VBFAQAUIXPRJAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(2-hydroxyethyl)fluorene-9-carboxylic acid 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以98%的产率得到9-<2-Hydroxy-ethyl>-fluorencarbonsaeure-(9)-lacton
  参考文献：
  名称：

  Studies on the Alkylation and Chlorination of Fluorenes: Preparation of 9-(2-Hydroxyethyl)fluorene and 2,7-Dichloro-9-(2-hydroxyethyl)fluorene

  摘要：

  描述了9-(2-羟乙基)氟烯（1）及其2,7-二氯衍生物2的大规模高效合成。氟烯及其2,7-二氯衍生物在9-烷基化反应中的反应性存在主要差异。这些差异归因于这些化合物的9位质子的酸性差异。此外，通过在精确控制的条件下，用NCS和浓盐酸在乙腈中处理，实现了氟烯及其衍生物的2,7-二氯化反应，结果令人满意。具体而言，需要高浓度的底物溶液和高温才能促进2,7-二氯化。

  DOI：

  10.1055/s-1994-25668
• 作为产物：
  描述：

  环氧乙烷 、 9-芴甲酸 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以78%的产率得到9-(2-hydroxyethyl)fluorene-9-carboxylic acid
  参考文献：
  名称：

  Studies on the Alkylation and Chlorination of Fluorenes: Preparation of 9-(2-Hydroxyethyl)fluorene and 2,7-Dichloro-9-(2-hydroxyethyl)fluorene

  摘要：

  描述了9-(2-羟乙基)氟烯（1）及其2,7-二氯衍生物2的大规模高效合成。氟烯及其2,7-二氯衍生物在9-烷基化反应中的反应性存在主要差异。这些差异归因于这些化合物的9位质子的酸性差异。此外，通过在精确控制的条件下，用NCS和浓盐酸在乙腈中处理，实现了氟烯及其衍生物的2,7-二氯化反应，结果令人满意。具体而言，需要高浓度的底物溶液和高温才能促进2,7-二氯化。

  DOI：

  10.1055/s-1994-25668

文献信息

• ESTER COMPOUND AND MEDICINAL USE THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP1479666A1

  公开（公告）日：2004-11-24

  A novel therapeutic agent for hyperlipidemia, which is an ester compound represented by the formula (1") (wherein    R1 and R2 are each hydrogen atom or optionally substituted aryl, etc.;    X is -COO- or -CON(R10)-;    R3 and R4 are each hydrogen atom, C1-C6 alkyl or C1-C6 alkoxy, etc.;    R5, R6 and R7 are each hydrogen atom, C1-C6 alkyl or C1-C6 alkoxy, etc.;    R8 and R9 are each independently hydrogen atom, C1-C6 alkyl, -CON(R18)(R19) or -COO(R20), etc.;    ring A, ring B and ring C are each independently aryl or heterocycle residue, etc.;    Alk1 and Alk2 are each independently alkanediyl, etc.;    l and m are each an integer of 0 or 1 to 3) or a prodrug thereof, or a pharmaceutically acceptable salt of either. The therapeutic agent selectively inhibits MTP in the small intestine, thus causes no such side effect as a fatty liver.

  一种治疗高脂血症的新型药物，其为酯化合物，由式(1")表示（其中：R1和R2均为氢原子或可选择取代的芳基等；X为-COO-或-CON(R10)-；R3和R4均为氢原子、C1-C6烷基或C1-C6烷氧基等；R5、R6和R7均为氢原子、C1-C6烷基或C1-C6烷氧基等；R8和R9各自独立地为氢原子、C1-C6烷基、-CON(R18)(R19)或-COO(R20)等；环A、环B和环C各自独立地为芳基或杂环残基等；Alk1和Alk2各自独立地为脂肪二亚基等；l和m均为0或1至3的整数），或其前药，或其药学上可接受的盐。该治疗剂能够选择性地抑制小肠中的MTP，因此不会引起脂肪肝等副作用。
• Ester compound and medicinal use thereof
  申请人：Hagiwara Atsushi

  公开号：US20050075367A1

  公开（公告）日：2005-04-07

  A novel therapeutic agent for hyperlipidemia, which is an ester compound represented by the formula (1″) (wherein R 1 and R 2 are each hydrogen atom or optionally substituted aryl, etc.; X is —COO— or —CON(R 10 )—; R 3 and R 4 are each hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, etc.; R 5 , R 6 and R 7 are each hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, etc.; R 8 and R 9 are each independently hydrogen atom, C 1 -C 6 alkyl, —CON(R 18 )(R 19 ) or —COO(R 20 ), etc.; ring A, ring B and ring C are each independently aryl or heterocycle residue, etc.; Alk 1 and Alk 2 are each independently alkanediyl, etc.; l and m are each an integer of 0 or 1 to 3) or a prodrug thereof, or a pharmaceutically acceptable salt of either. The therapeutic agent selectively inhibits MTP in the small intestine, thus causes no such side effect as a fatty liver.

  一种治疗高脂血症的新型药物，其为酯化合物，由式（1”）所表示（其中，R1和R2分别为氢原子或可选取代的芳基等；X为—COO—或—CON(R10)—；R3和R4分别为氢原子、C1-C6烷基或C1-C6烷氧基等；R5、R6和R7分别为氢原子、C1-C6烷基或C1-C6烷氧基等；R8和R9分别独立地为氢原子、C1-C6烷基、—CON(R18)(R19)或—COO(R20)等；环A、环B和环C分别独立地为芳基或杂环残基等；Alk1和Alk2分别独立地为脂肪二亚基等；l和m分别为0或1至3的整数），或其前药，或其药学上可接受的盐。该治疗剂能够选择性地抑制小肠中的MTP，从而不会引起脂肪肝等副作用。
• ESTER COMPOUND AND MEDICAL USE THEREOF
  申请人：Hagiwara Atsushi

  公开号：US20100158996A1

  公开（公告）日：2010-06-24

  A novel therapeutic agent for hyperlipidemia, which is an ester compound represented by the formula (1″) (wherein R 1 and R 2 are each hydrogen atom or optionally substituted aryl, etc.; X is —COO— or —CON(R 10 )—; R 3 and R 4 are each hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, etc.; R 5 , R 6 and R 7 are each hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, etc.; R 9 and R 9 are each independently hydrogen atom, C 1 -C 6 alkyl, —CON(R 18 ) (R 19 ) or —COO(R 20 ), etc.; ring A, ring B and ring C are each independently aryl or heterocycle residue, etc.; Alk 1 and Alk 2 are each independently alkanediyl, etc.; l and m are each an integer of 0 or 1 to 3) or a prodrug thereof, or a pharmaceutically acceptable salt of either. The therapeutic agent selectively inhibits MTP in the small intestine, thus causes no such side effect as a fatty liver.

  一种治疗高脂血症的新型药物，其为酯化合物，由式（1″）所表示（其中R1和R2分别为氢原子或可选择取代的芳基等；X为—COO—或—CON(R10)—；R3和R4分别为氢原子、C1-C6烷基或C1-C6烷氧基等；R5、R6和R7分别为氢原子、C1-C6烷基或C1-C6烷氧基等；R8和R9分别独立地为氢原子、C1-C6烷基、—CON(R18)(R19)或—COO(R20)等；环A、环B和环C分别独立地为芳基或杂环残基等；Alk1和Alk2分别独立地为脂肪二亚基等；l和m分别为0或1至3的整数），或其前药，或其药学上可接受的盐。该治疗剂选择性地抑制小肠中的MTP，从而不会引起脂肪肝等副作用。
• US7625948B2
  申请人：——

  公开号：US7625948B2

  公开（公告）日：2009-12-01
• Studies on the Alkylation and Chlorination of Fluorenes: Preparation of 9-(2-Hydroxyethyl)fluorene and 2,7-Dichloro-9-(2-hydroxyethyl)fluorene
  作者：John Perumattam、Charley Shao、William L. Confer

  DOI：10.1055/s-1994-25668

  日期：——

  Efficient large-scale syntheses of 9-(2-hydroxyethyl)fluorene (1) and its 2,7-dichloro derivative 2 are described. Major differences exist in the reactivity of fluorene and its 2,7-dichloro derivative toward 9-alkylation. These differences are attributed to the difference in acidity of the protons in the 9-position of these compounds. Also 2,7-dichlorination of fluorene and its derivatives was satisfactorily achieved by treatment with NCS and conc. HCl in acetonitrile under carefully controlled conditions. Specifically, a highly concentrated solution of substrates and elevated temperatures were required for facile 2,7-dichlorination.

  描述了9-(2-羟乙基)氟烯（1）及其2,7-二氯衍生物2的大规模高效合成。氟烯及其2,7-二氯衍生物在9-烷基化反应中的反应性存在主要差异。这些差异归因于这些化合物的9位质子的酸性差异。此外，通过在精确控制的条件下，用NCS和浓盐酸在乙腈中处理，实现了氟烯及其衍生物的2,7-二氯化反应，结果令人满意。具体而言，需要高浓度的底物溶液和高温才能促进2,7-二氯化。