2,3-dihydro-1H-naphtho<2,1-b>thiopyran-1-one | 3528-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dihydro-1H-naphtho<2,1-b>thiopyran-1-one
• 英文别名: 2,3-dihydro-1H-benzo[f]thiochromen-1-one；5,6-benzothiochromanone；2,3-dihydro-benzo[f]thiochromen-1-one；2,3-Dihydro-benzo[f]thiochromen-1-on；1H-2,3-Dihydro-naphtho<2.1-b>thiopyran-1-on；2,3-Dihydro-benzo[f]thiochromen-1-one；2,3-dihydrobenzo[f]thiochromen-1-one
• CAS: 3528-20-9
• 化学式: C₁₃H₁₀OS
• mdl: MFCD00156719
• 分子量: 214.288
• InChiKey: ZFGBYVYXAMNRCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-1H-naphtho<2,1-b>thiopyran-1-one 在 N,N-二甲基硫代甲酰胺 、 三氟化硼乙醚 、 乙酸酐 、 三氯氧磷 作用下， 反应 6.0h， 生成 3-methyl-4H,5H-naphtho<1',2':5,6>thiopyrano<4,3-b>pyran-4-thione
  参考文献：
  名称：

  Takido, Toshio; Tomizawa, Nobuyuki; Tsukano, Kazuo, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 841 - 846

  摘要：

  DOI：
• 作为产物：
  描述：

  3-[2]naphthylsulfanyl-propionitrile 在 硫酸 作用下， 生成 2,3-dihydro-1H-naphtho<2,1-b>thiopyran-1-one
  参考文献：
  名称：

  Aminoalkanol Derivatives of Benzo(f)chroman^1,2

  摘要：

  DOI：

  10.1021/ja01202a027

文献信息

• Intramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol
  作者：Hashim F. Motiwala、Rakesh H. Vekariya、Jeffrey Aubé

  DOI：10.1021/acs.orglett.5b02851

  日期：2015.11.6

  Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel–Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential

  芳基烷基酰氯在1,1,1,3,3,3-六氟-2-丙醇中的简单溶解可促进分子内Friedel-Crafts酰化反应，而无需其他催化剂或试剂。该反应在操作和产物分离上都操作上很简单（只需要浓缩后再纯化），并适用于各种各样的底物。据报道涉及潜在反应机理的初步研究。
• Synthesis and Biochemical Evaluation of Thiochromanone Thiosemicarbazone Analogues as Inhibitors of Cathepsin L
  作者：Jiangli Song、Lindsay M. Jones、G. D. Kishore Kumar、Elizabeth S. Conner、Liela Bayeh、Gustavo E. Chavarria、Amanda K. Charlton-Sevcik、Shen-En Chen、David J. Chaplin、Mary Lynn Trawick、Kevin G. Pinney

  DOI：10.1021/ml200299g

  日期：2012.6.14

  by chemical synthesis and evaluated as inhibitors of cathepsins L and B. The most promising inhibitors from this group are selective for cathepsin L and demonstrate IC50 values in the low nanomolar range. In nearly all cases, the thiochromanone sulfide analogues show superior inhibition of cathepsin L as compared to their corresponding thiochromanone sulfone derivatives. Without exception, the compounds

  通过化学合成制备了一系列36个主要在C-6位官能化的包含硫代苯并二氢吡喃酮分子骨架的thiosemicarbazone类似物，并将其评估为组织蛋白酶L和B的抑制剂。该组中最有希望的抑制剂对组织蛋白酶L具有选择性，并显示出IC50值在低纳摩尔范围内。在几乎所有情况下，硫代苯并二氢吡喃酮硫化物类似物均比其相应的硫代苯并二氢吡喃酮砜衍生物具有更好的组织蛋白酶L抑制作用。毫无例外，所评估的化合物对组织蛋白酶B无活性（IC50> 10000 nM）。最有效的组织蛋白酶L抑制剂（IC50 = 46 nM）被证明是6,7-二氟类似物4。小分子已知的结构-活性关系，
• An effective synthesis of fused cyclic thiopyrans and pyrans by molybdenum(VI) sulfide catalyzed reduction of the corresponding thiopyranones and pyranones
  作者：Toshio Takido、Kunio Itabashi、Yuzuru Takagi

  DOI：10.1002/jhet.5570320252

  日期：1995.3

  The synthesis of fused cyclic dihydrothiopyrans 2a-c from dihydrothiopyranones 1a-c and thiopyrans 2d-f from thiopyranones 1d-f by catalytic reduction over molybdenum(VI) sulfide (MoS3) has been studied. The hydrogenolysis of the carbonyl group of 1a-f over MoS3 catalyst proceeded selectively to give the corresponding 2a-f in high yields. Neither alcohols nor olefins were not detected in the products

  稠环dihydrothiopyrans的合成2a-c中从dihydrothiopyranones 1A-1C和噻喃2D-F从thiopyranones 1d的-F通过催化还原钼（VI）硫化物（MOS 3）进行了研究。1a-f的羰基在MoS 3催化剂上的氢解选择性进行，以高收率得到相应的2a-f。产品中均未检测到醇或烯烃。该方法也成功地用于由二氢吡喃酮1h和吡喃酮1g合成二氢吡喃2h和吡喃2g 。
• Carcinogenic nitrogen compounds. Part LXV. New mono- and di-benzo-derivatives of [1] benzothiopyrano[4,3-b]indole
  作者：N. P. Buu-Hoï、P. Jacquignon、A. Croisy、A. Loiseau、F. Périn、A. Ricci、A. Martani

  DOI：10.1039/j39690001422

  日期：——

  The previously reported synthesis of [1]benzothiopyrano[4,3-b]indoles from the arylhydrazones of appropriate thiochroman-4-ones has been extended to diversely substituted thiochroman-4-ones to give a number of mono-and di-benzo-derivatives of this pseudoazulene, which are of potential biological interest as potential carcinogens or enzyme-inducers.

  先前报道的由合适的硫代色烷-4-酮的芳基hydr合成[1]苯并硫代吡喃并[4,3- b ]吲哚的过程已扩展到不同取代的硫代色烷-4-酮，从而得到许多单-和二-苯并-该假氮杂烯的衍生物，作为潜在的致癌物或酶诱导剂具有潜在的生物学意义。
• Synthesis of geometrically defined exocyclic olefins
  作者：Youssef L. Bennani、C.-K. Hwang、Stacie S. Canan Koch、Kristin S. Marron、Laura J. Dar-ti、Beth-Ann Badea、Alex M. Nadzan

  DOI：10.1016/0040-4039(96)01885-0

  日期：1996.11

  bicyclic and tricyclic ketones with lithium ethynyl acetylide, followed by the addition of a catalytic amount of CSA or p-TSA, affords the corresponding exocyclic olefinic ester in good yields, and geometric ratios up to 13:1 favoring the cis olefin. This procedure represents an addition to the repertoire of olefination methods and can readily be extended to other cyclic and acyclic systems.

  用乙炔基乙炔化锂处理双环和三环酮，然后加入催化量的CSA或p-TSA，可得到高产率的相应环外烯烃酯，且几何比高达13：1，有利于顺式烯烃。该方法是对烯烃化方法的补充，可以很容易地扩展到其他环状和非环状体系。