摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

(10R, 11R)-(+)-squalene-10, 11-epoxide | 109009-55-4

中文名称
——
中文别名
——
英文名称
(10R, 11R)-(+)-squalene-10, 11-epoxide
英文别名
10(R),11(R)-Oxidosqualene;(2R,3R)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-2-methyl-3-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]oxirane
(10R, 11R)-(+)-squalene-10, 11-epoxide化学式
CAS
109009-55-4
化学式
C30H50O
mdl
——
分子量
426.726
InChiKey
OZBVWSJPTAXJQA-FRBKMBEASA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    10.4
  • 重原子数:
    31
  • 可旋转键数:
    15
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.67
  • 拓扑面积:
    12.5
  • 氢给体数:
    0
  • 氢受体数:
    1

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • Internal Oxidosqualenes: Determination of Absolute Configuration and Activity as Inhibitors of Purified Pig Liver Squalene Epoxidase
    作者:Jose-Luis Abad、Josefina Casas、Francisco Sanchez-Baeza、Angel Messeguer
    DOI:10.1021/jo00117a014
    日期:1995.6
    The preparation and characterization of oxidosqualenes 3-(6R,7R), 3-(6S,7S), 4-(10R,11R), and 4-(10S,11S) is reported. Squalenediol 6 was converted into the corresponding mixture of(R)-Mosher esters 8 and 9, which were separated by semipreparative HPLC. Esters 8 and 9 were reduced to the chiral diols 6-(6R,7S) and 6-(6S,7R), respectively, which were finally converted into the corresponding epoxides 3-(6R,7R) and 3-(6S,7S). A similar procedure was used for the preparation of chiral epoxy derivatives 4-(10R,11R) and 4-(10S,11S) from esters 10 and 11, respectively. The determination of the absolute configuration of these epoxides was carried out by using the method reported by Ohtani et al. (J. Am. Chem. Sec. 1991, 113, 4092), which was adapted to the case of racemic mixtures from synthetic origin. For this purpose, the (R)-Mosher esters derived from the enantiomers of squalenediols 6 or 7 were used. The validity of this approach was confirmed by the absolute configuration found for the three squalenediols 6-(6R,7R), 6-(6S,7S), 7-(10R,11R), and 7-(10S,11S) formed in the Sharpless asymmetric dihydroxylation of squalene (Crispino, G. A.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 4273). Results on the inhibitory activity of oxidosqualenes 3-(6R,7R), 3-(6S,7S), 4-(10R,11R), and 4-(10S,11S) using purified squalene epoxidase (SE) fi om pig liver showed that epoxide 3-(6S,7S) was the best inhibitor within the compounds assayed (IC50 = 6.7 mu M), although oxidosqualene 4-(10R,11R) also exhibited a moderate inhibitory activity (IC50 = 25 mu M). The inhibition elicited by the epoxy derivative 3-(6S,7S) was competitive with respect to squalene (K-i = 2.7 mu M). This activity is comparable to that reported for the most potent competitive SE inhibitors described so far. Finally, incubation of oxidosqualene 3-(6S,7S) with purified SE led to the formation of dioxidosqualene 22-(3S,6S,7S), whereas its regioisomer 23-(3S,18S,19S) was not detected. In contrast, incubation of epoxide 3-(6R,7R) under the same conditions afforded a mixture of dioxides 22-(3S,6R,7R) and 23-(3S,18R,19R) in a 5:12 molar ratio. The fact that oxidosqualenes 3 and 4 have been found in nature, and our previous results showing that racemic dioxide 23 is a potent inhibitor of oxidosqualene-lanosterol cyclase in rat liver microsomes (Abad, J. L.; et al. J. Org. Chem. 1993, 58, 3991), confers a potential physiological relevance to the results reported herein.
  • (10 , 11 )-(+)-squalene-10, 11-epoxide: Isolation from and the asymmetric synthesis
    作者:Hideo Kigoshi、Makoto Ojika、Yoshikazu Shizuri、Haruki Niwa、Kiyoyuki Yamada
    DOI:10.1016/0040-4039(82)80144-5
    日期:——
    From a red alga Laurencia okamurai (10R̃, 11R̃)-(+)-squalene-10, 11-epoxide 1̃ was isolated and its asymmetric synthesis has been achieved starting from trans, trans-farnesol.
    从红藻Laurencia okamurai(10R 4,11R 4)-(+)-角鲨烯-10中,分离出11-环氧化物1 4,并从反式,反式-法尼醇开始实现了其不对称合成。
查看更多

同类化合物

(5β,6α,8α,10α,13α)-6-羟基-15-氧代黄-9(11),16-二烯-18-油酸 (3S,3aR,8aR)-3,8a-二羟基-5-异丙基-3,8-二甲基-2,3,3a,4,5,8a-六氢-1H-天青-6-酮 (2Z)-2-(羟甲基)丁-2-烯酸乙酯 (2S,4aR,6aR,7R,9S,10aS,10bR)-甲基9-(苯甲酰氧基)-2-(呋喃-3-基)-十二烷基-6a,10b-二甲基-4,10-dioxo-1H-苯并[f]异亚甲基-7-羧酸盐 (+)顺式,反式-脱落酸-d6 龙舌兰皂苷乙酯 龙脑香醇酮 龙脑烯醛 龙脑7-O-[Β-D-呋喃芹菜糖基-(1→6)]-Β-D-吡喃葡萄糖苷 龙牙楤木皂甙VII 龙吉甙元 齿孔醇 齐墩果醛 齐墩果酸苄酯 齐墩果酸甲酯 齐墩果酸乙酯 齐墩果酸3-O-alpha-L-吡喃鼠李糖基(1-3)-beta-D-吡喃木糖基(1-3)-alpha-L-吡喃鼠李糖基(1-2)-alpha-L-阿拉伯糖吡喃糖苷 齐墩果酸 beta-D-葡萄糖酯 齐墩果酸 beta-D-吡喃葡萄糖基酯 齐墩果酸 3-乙酸酯 齐墩果酸 3-O-beta-D-葡吡喃糖基 (1→2)-alpha-L-吡喃阿拉伯糖苷 齐墩果酸 齐墩果-12-烯-3b,6b-二醇 齐墩果-12-烯-3,24-二醇 齐墩果-12-烯-3,21,23-三醇,(3b,4b,21a)-(9CI) 齐墩果-12-烯-3,11-二酮 齐墩果-12-烯-2α,3β,28-三醇 齐墩果-12-烯-29-酸,3,22-二羟基-11-羰基-,g-内酯,(3b,20b,22b)- 齐墩果-12-烯-28-酸,3-[(6-脱氧-4-O-b-D-吡喃木糖基-a-L-吡喃鼠李糖基)氧代]-,(3b)-(9CI) 鼠特灵 鼠尾草酸醌 鼠尾草酸 鼠尾草酚酮 鼠尾草苦内脂 黑蚁素 黑蔓醇酯B 黑蔓醇酯A 黑蔓酮酯D 黑海常春藤皂苷A1 黑檀醇 黑果茜草萜 B 黑五味子酸 黏黴酮 黏帚霉酸 黄黄质 黄钟花醌 黄质醛 黄褐毛忍冬皂苷A 黄蝉花素 黄蝉花定